Fall is here, and the chance to refresh your wardrobe with the season's newest trends has arrived. This transitional period can be a bit stressful if you're like many. After all, no one wants to get stuck wearing the same boring, recycled outfits they've worn for the last three years. The good news is that preppy style is back and better than ever, providing a sophisticated yet versatile palette to work from this fall. Whether you're searching for the perfect preppy aesthetic or just looking to add a few preppy touches, this blog will explore the ins and outs of preppy style, from its classic elements and fresh modern updates to how you can incorporate it into your wardrobe for a chic fall refresh.

WhatColors’ AI personal color analysis app can help you identify your ideal colors for this trend. By focusing on shades that complement your unique coloring, you can create balanced and visually appealing preppy outfits that are sure to elevate your fall style.

Table of Contents

• What Is the Preppy Style?

• 5 Signs You Have A Preppy Style Personality

• The Evolution of Preppy Style, From the 1800s to Today

• 12 Tips to Nail the Preppy Style in 2024

• The Ultimate Preppy Style & Clothes Primer for Men

• 7 Modern Women's Preppy Style Tips And 14 Ways to Implement Them Into Your Look

• 15 Must-Have Items for a Preppy, Girly, and Sophisticated Back-To-School Wardrobe

• Do Preppy Girls Wear Jeans?

• 43 Preppy Clothing Brands That Will Elevate Your Wardrobe

• 5 Ways to Dress Preppy on Any Budget

• Try AI Personal Color Analysis For Free Today

What Is the Preppy Style?

Preppy style has its roots in the early 20th century when the children of wealthy families wore neat, classic clothes to attend private preparatory schools in New England. These institutions focused on getting students ready for Ivy League colleges, and the distinct style that emerged reflected the schools’ elite status and the old-money families that sent their kids there. 

As you can imagine, this kind of dressing wasn’t exactly affordable. The look included high-quality materials and tailored pieces, like blazers, button-downs, and pleated skirts that conveyed tradition and privilege. Over the years, the preppy style has evolved, but its origins remain relevant, and its associations with wealth and elitism persist. 

What Are the Key Elements of Preppy Style? 

Regarding preppy style, think classic, polished, and timeless. You won’t find any loud graphic tees or overly distressed denim here. Instead, key elements of the aesthetic include:

• Clean lines: Preppy style is all about looking put together, so it’s no surprise that the aesthetic favors garments that look good on a yacht. 

• Bright colors: You can stick with neutrals like navy or cream. But preppy style comes to life with vibrant hues, especially pastels and brights. 

• Patterns: From plaids to stripes, festive motifs add personality to preppy outfits.

• High-quality materials: To achieve the signature polished look of preppy style, choose clothes made of quality fabrics, such as cotton, linen, and wool. 
  
  

How to Style Preppy Looks for Different Occasions 

One of the best things about preppy style is its versatility. Outfits can easily be tailored to suit casual settings, like brunch, and more formal affairs, such as weddings. To achieve a laidback preppy look, consider:

• Fresh pair of white sneakers

• Straight-leg jeans

• Short-sleeve button-down or a polo shirt
  
  

Layer on a lightweight knitted vest or a cardigan to make the look more interesting. For chillier days, swap the jeans for chinos or corduroys in a fun color and add a few accessories, like a baseball cap or a canvas tote. To transition the look for a more formal occasion, replace the sneakers with loafers and the cardigan with a tailored blazer.

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5 Signs You Have A Preppy Style Personality

Preppy style is about the classic, clean-cut look that reminds you of a collegiate campus. This style has roots in the elite Northeastern school, and it’s no wonder it evokes charm and sophistication. Preppy style is also occasionally referred to as academic style, and for good reason. As much as it channels an upper-crust aesthetic, it’s also a practical and functional look that’s great for studying and getting through life on campus. 

Preppy style has a lot in common with classic style, so you may well find that you are drawn to elements of both. Preppy style can also draw inspiration from natural style. As a preppy style personality, you love cozy knits, checks, and stripes and prefer to wear flat shoes and natural fibers, including leather and wool. 

1. You Appreciate Clean-Cut Styles

We won’t find you in distressed jeans or a moto jacket. Instead, you prefer a blazer, a V-neck sweater, and a classic jeans style like bootcut or straight-leg. If you love a preppy aesthetic, you’re in luck, as preppy style and check prints are very much on trend at the moment.

2. You Aren’t Trend Obsessed

It’s much more important to you to have a good closet of essentials than to shop for a statement piece each season. 

3. You Have A Lot Of Stripes

If you have one pattern in your closet, it will be striped. That’s because, as well as being college-inspired, the preppy look also nods to the nautical.

4. You Love A Dress Or Shirt With A Collar

While you’ll wear t-shirts and boat necks, collared clothing styles such as the Peter Pan collar, classic button-down shirt or shirt dress, and the polo style are among your favorite looks.

5. You Don’t Have A Preference For Pants Or Skirts

While preppy style is generally comfortable, you are just as at home in a pair of pants as you are in a skirt, and you probably have equal numbers of each in your closet. 

Discover Your Perfect Palette

WhatColors helps you find what colors to wear based on your skin tone. Finally, our patented color match technology lets you get your season based on your skin tone. Get the perfect colors based on your season. Avoid colors that are a definite no. Based on your skin, eye, and hair color, find the perfect nail colors with our WhatColors nail color generator.

Get your color analysis done within 60 seconds with WhatColors’ AI personal color analysis app. Download our app for free today on the App Store or Google Play store.

The Evolution of Preppy Style, From the 1800s to Today

Preppy style emerged in the late 1800s and early 1900s as a status symbol worn by wealthy boys attending preparatory and Ivy League schools. The name derived from prep short for preparatory and was popularized in the 1970s to describe the affluent, East Coast lifestyle depicted in the media. 

Brooks Brothers, who opened their doors in 1818, laid the foundation for classic American preppy style. The brand's button-down shirts, knit sweaters, and loafers were all part of their closet must-haves. By the 1930s, college women were in on it too. Once the first pair of "Lady Levi's" were released in 1934, jeans became a major part of preppy style—and we never looked back. 

The '50s: The Decade That Expanded Preppy Style

In the 1950s, the preppy trend expanded even more. Just think about your favorite movies set in that decade. Whether it's Grease or Pleasantville, there are so many twin sets or sweaters styled over collared shirts—and not just on school kids either. 

At the same time, a few changes were happening. Sporty rugby shirts, worn off-field then, were thrown in the mix, while plaid became even more popular. Bowling shirts and denim created a branch of preppy called Americana, and there was also that whole tighter, sexier, pin-up look. 

The '80s: The Birth of the Classic Look

Once we reached the '80s, preppy style as we now know it really began to form—thanks to a book called The Official Preppy Handbook. Initially, it was meant to be humorous and tongue-in-cheek, but according to The New York Times, it sold more than a million copies. 

The guide inspired people to wear khakis, plaid blazers, and knotting sweaters over their shoulders unironically. While these clothes had been a sign of privilege in the '50s, they were being made for the masses now, thanks to the rise of Tommy Hilfiger, Calvin Klein, and Lacoste. With their turtlenecks and tartan blazers, Brooke Shields and Princess Diana are certainly preppy icons of the decade. 

The '90s: A Shrinking Twist on Preppy Style

The late '90s brought a new, shrunken twist to preppy style. Pants styles were lower, boot-cuts were in, and Britney Spears turned looking like a sexy school girl—complete with a white button-down and pleated skirt—into a major thing. Plus, while oversized grunge had a moment during this decade, you can argue that some preppy elements—like all the plaid and knotting shirts (this time, around your waist) were still there. 

It was prep, new millennium-style, and J.Crew was hitting its stride. People wanted those nautical rolled-neck sweaters and envisioned themselves looking like a cast member of Dawson's Creek. (The cast really did appear in a 1998 J. Crew catalog.) 

The 2000s: A New Era for Preppy Style

Jenna Lyons took her role as J.Crew's creative director and began shaking things up in 2008. Lyons made us think of preppy style as shockingly bright colors, tons of sparkle, and playful twists. Things became less Nantucket and more fashion-girl-approved. 

Eventually, another shift occurred, and athleisure arrived on the scene. By 2015, the comfy joggers and leggings worn by off-duty models looked more appealing than any button-up, and black was back. 

The "New" Preppy Look

During Fashion Week, collections clarified that the preppy style has undergone yet another metamorphosis.

• Chloé and Michael Kors featured mid-length skirt suits

• Burberry had collegiate sweaters

• Versace broke out the rugby stripes

• Dior included a ton of plaid and neckties
  
  

Those styles have already hit the streets as people are back knitting their sweaters and reaching for pairs of chinos. We're seeing collars again, vests, and argyle, which are other iconic preppy prints. 

12 Tips to Nail the Preppy Style in 2024

1. Choose 1 or 2 Solid Colors to Ground Your Preppy Look

When you think of preppy style, it can feel overwhelming. There are so many elements that you can combine to create a classic sophisticated look. Start by selecting a couple of solid pieces to ground your outfit. Look for colors commonly associated with preppy style to create a base for your outfit like:

• Navy

• Khaki

• White
  
  

Pick a few other complementary colors for your look. For example, if you're wearing red chinos, style them with a blue shirt or a white shirt with a charcoal gray trench coat or jacket. Don't be afraid to play with preppy colors! A pop of color can balance your neutral pieces to make your whole look more interesting. 

2. Add a Preppy Print for Visual Interest

Prints can instantly transform an outfit from minimalist or modern to preppy. To achieve an effortlessly preppy look, stick to a simple formula of 2 solid colors or neutrals and 1 patterned item. 

For example, wear a plaid shirt with cream-colored trousers or wear a blue gingham tunic with a khaki skirt. Paisley, tweed, and nautical prints are all staples in a preppy wardrobe. Try wearing a navy striped shirt tucked into fitted jeans and wear a navy quilted jacket. 

3. Wear Khaki Trousers or a Skirt

Khaki is a preppy must-have—a stylish option for casual, everyday outfits, and you can wear it to dressy functions. Pair khaki with any preppy top or jacket since it works with anything! Buy a pair of tailored khaki pants or a stylish knee-length khaki skirt. If you want to round out your summer wardrobe, pick up a pair of khaki shorts, too. 

To style your khakis, pair a skirt or trousers with a plain leather belt and a crisp fitted shirt or polo. To dress up your preppy khaki outfit, throw on a fitted blazer and wear nice leather shoes or pumps. 

4. Invest in Simple Pieces for Your Wardrobe

Preppy outfits are relatively simple—they include a few classic items. This makes it easy to look preppy! Once you build a basic wardrobe, you can create dozens of outfits. Stock up on these essentials to get started: 

• Tunics Tailored trousers or skirts

• Button-down shirts or blouses Polos

• Oxford shirts navy suits or blazers sweaters trench coat 
  
  

5. Choose Neutral Colors as the Base for Your Outfit

Navy, white, and khaki are great colors for preppy clothes. They're really easy to pair with brighter colors or preppy prints and look great on everyone. For example, pick up a navy blazer and a white shirt. Black can be a preppy color if you use it sparingly. Save it for formal looks like a fitted black blazer with a khaki skirt, crisp white shirt, and emerald green pumps or leather loafers. 

6. Choose a Statement Sweater

Go for a cabled or argyle sweater to create a cozy, winter look. Preppy looks aren't just for the summer. For cold-weather preppy style, pop on a cashmere sweater in a solid color over a button-down shirt. To add interest, you could wear a cabled knit sweater or an argyle sweater with a colorful diamond pattern. Don't forget that a solid cardigan is also a timeless preppy piece. Throw it over your shoulder if it's cool out, or toss on a sleeveless V-neck sweater. 

7. Avoid Wearing Revealing Clothing

Stick to a simple conservative outfit that doesn't show much skin. Think simple, clean, and classic when you think of a preppy style. For instance, if you want to wear a skirt, pick a knee-length skirt instead of a mini-skirt. Choose tops with sleeves or short sleeves to provide a little coverage. For a casual look with coverage, pair a colorful tunic with khaki chinos. 

8. Keep Your Hair Sleek and Brushed

If you wear short hair, comb it back and part it along the side. For a little volume, style it up into a pompadour. Pull it back into a ponytail or a low bun at the nape of your neck for longer hair. 

Remember that your hairstyle is one more way to make your preppy look unique! Headbands and bows are cute, preppy hair accessories you can play around with. Style your hair with matte pomade or shiny gel to keep your perfectly coiffed hair in place all day. 

9. Go for Conservative Footwear

Pair your outfit with loafers, flats, or boat shoes. Preppy shoes should look functional, comfortable, and classic. Loafers, moccasins, and duck boots are great for men, while women could wear flats, boat shoes, duck boots, or nude heels. Match your shoes to the occasion. Wear nice loafers or kitten heels if you're looking preppy at an evening event. Wear something comfortable like boat shoes or a pair of flats if you're dressing for work. 

10. Keep Accessories Classic or Minimal

Wear bowties or belts to complement your outfit. If you're wearing a button-down shirt, consider wearing a fun bowtie or a bold striped tie to add interest. Belts are also a great preppy accessory—choose a plain leather belt to wear with your trousers, skirt, or jeans. 

Break out your sunglasses for a fun accessory. Choose vintage styles like large circular sunglasses or aviators if you'd like a personalized preppy accessory, shop for a monogrammed belt buckle. 

11. Wear Modest, Elegant Jewelry

Choose pieces like pearls, simple cufflinks, or watches. You don't want flashy, glamorous jewelry to distract from the tailored look you've put together. Stock your wardrobe with pearl earrings, necklaces, and bracelets, or pick up gold or nautical cufflinks if you frequently wear suits. A great watch is never out of place, either! 

12. Preppy Patterns

The most popular patterns for girls include argyle and plaid. If you are a girl you can wear plaid skirts and tops. You can also wear an argyle sweater vest. Also, wearing a tweed jacket and a tweed skirt is very preppy. If you are a boy, popular patterns are plaid, argyle, and stripes. Wearing a plaid shirt is an option you can also wear an argyle or striped sweater vest.

The Ultimate Preppy Style & Clothes Primer for Men

If you’re looking to create or expand a preppy wardrobe, these are the top must-have items to search for. While a lot of retailers will offer versions of preppy style staples, you’ll likely find some of the best things are in thrift or second-hand stores, listed on eBay or Etsy, or at estate sales. 

Preppy Style Jackets and Blazers

This is perhaps the most iconic piece of menswear worn and designed to be worn by preps. Although available in a variety of styles, the standard is a navy single-breasted jacket with notched lapels and three brass buttons, often with an icon or logo that is nautical in nature or represents the brand. 

You can always go for the double-breasted look for an increased nautical feel. Of course, many companies make these blazers, but the most popular today are from Ralph Lauren and Brooks Brothers.

Preppy Style Shirts 

Oxford Button Down Shirts

Button-down collars were initially introduced by Brooks Brothers in 1896 and have remained popular as a way of dressing down a regular dress shirt. Using buttons that fasten down the collar points on the front of the shirt meant these were almost exclusively worn as sport shirts until the mid-1950s. 

Still considered a sports shirt in most circles, or as a way to give casual flair to elegant attire, these shirts are extremely popular in prep culture and are often paired with the iconic navy blazer and a repp tie. 

Polo Shirts

Polo shirts, which can also be referred to as golf or tennis shirts, are a well-known staple in prep style. A casual and soft shirt with a collar, a placket, and usually two or three buttons, it can often feature a breast pocket as well. Made from knitted piqué cotton, it can also be found in silk, merino wool, or various synthetic materials. These shirts are often worn with a pair of shorts or trousers but can also be paired with a blazer or sports jacket. 

Preppy Style Trousers and Pants 

Chinos

Chinos are trousers made from a twill fabric, originally 100% cotton. While they can be found in synthetic blends now, the best are still made of cotton. Brooks Brothers offers a superior selection of them, as do many other fine clothiers. Today, they come in many colors, but the most common is khaki, which is still very popular in coastal culture. 

GTH (Go To Hell) Pants

GTH pants take some serious getting used to. This is a style of its own and one that will surely net you either looks of disdain or nods of approval as you walk around in them. These are bright pants with sometimes bold embroideries on them of sailboats, anchors, lobsters, crabs, frogs, and a variety of other icons. 

They are obnoxious but so much fun to wear! Brooks Brothers once said that it’s like playing a game of chicken with your friends except no one goes off a cliff. Instead, the winner is viewed as the most daring dresser around. Just use some caution with what you pair with them. 

Nantucket Reds

Nantucket Reds are an essential component of prep culture. The red pants, shorts, shirts, hats, and various other articles were originally distributed by Murray’s Toggery Shop in Nantucket and are guaranteed to fade to an almost rosy pink.

They are traditionally pants, but today, they consist of an entire selection of clothing and accessories that are incredibly popular to the point of being legendary in Martha’s Vineyard, Cape Cod, and their birthplace of Nantucket. 

Preppy Style Knitwear 

Argyle Sweaters

The argyle sweater is predominantly seen in golf apparel, which is why it has become so ingrained in the prep culture. Since golf has long been a favorite pastime of preppies, Argyle has become a pattern fashionable amongst both men and women. 

The pattern itself can simply be characterized as being made up of diamonds or lozenges. Typically they will overlap in a motif which can add a sense of multiple dimensions and texture. In most cases, it’s used as an overlay of intercrossing diagonal lines on solid diamonds.  

Cable Knit Sweaters

Cable-knit sweaters are classic and will never go out of style. Whether they are made of cotton, wool, or cashmere, with sleeves or without, they are a staple of a preppy wardrobe. If you wear bow ties, a crew neck is the way to go, while ties look great with V-neck sweaters. For a soft, casual outfit, look for a melange two-tone yarn, which lends the sweater a mottled, gentle look. 

Rugby Shirts

Although Rugby is quintessentially British, many preps like to wear rugby shirts probably because the aesthetic of bold colorful stripes and a white collar is very much in line with other preppy clothing items. 

Tennis & Cricket Sweaters

Tennis or Cricket sweaters are a must-have in a preppy wardrobe. Take a look at our dedicated Tennis sweater article here. 

Preppy Style Footwear 

Boat Shoes

Like many staples in prep style, you either love boat shoes or hate them. While many credit Sperry Topsider with the initial introduction, and most people consider them the quintessential boat shoe, there are many companies today that make them. Boat shoes are pretty much exactly what they sound like. They were created as a non-slip shoe for sailing and are generally made of leather but can be crafted from other materials such as canvas. They are typically worn without socks as a casual shoe, and as such are tied using leather boat shoelaces. 

Loafers

Loafers, like boat shoes, are synonymous with coastal culture. There are a variety of loafers on the market, from the most casual to semi-dress shoes. They are typically categorized as low, lace-less shoes that you slip on and wear out rather than as slippers indoors. 

Traditionally, loafers are a casual shoe, but recently many preps have begun wearing them with lounge suits or to work at offices with a more relaxed dress code. They come in a variety of styles, colors and materials and occasionally will feature tassels or decorations on the front of the shoe. For a detailed discussion of loafers in all their varieties, read the Ultimate Loafer Guide. 

L.L. Bean Boots

Founded in 1912 by Leon Leonwood Bean, they quickly became known for their boots. Originally, they were hunting boots made of rubber and organically treated full-grain cowhide to resist water. A crepe rubber sole and contrasting brown or tan uppers achieved the characteristic look. While most boots today are lined with Gore-Tex, back then, a simple wool lining was the norm. 

Many would give an arm and a leg to find new old stock boots in their size, but even the current version of their boots is so popular that the annual sales of the company are north of 1.5 billion. Of course, they now sell all kinds of other outdoor-related items, but the Bean boots in different heights and variations are still a favorite with preps. 

White Shoes

White buckskin shoes, also known as white bucks, are a popular preppy companion to seersucker pants, cocktail parties, horse races, or anything else related to summer. Paired with linen, chinos, or seersucker, they provide the wearer with a debonair, seasonally appropriate look. Buckskin leather is technically from the male deer, but today, cowhide is often used instead because it is less expensive and more widely available. 

In the U.S. most buckskin shoes show the backside of the leather, which has a texture similar to suede, but the front side of buckskin leather can be very nice as well. Many white bucks come with a lightweight, red rubber sole although they can also be found with classic leather soles in the Goodyear construction. 

Preppy Style Outerwear 

Barbour Wax Jacket

Barbour wax jackets are extremely popular with Prep’s, and they have been for years. Most people choose between the Beaufort, which was designed for shooting with an extra game pocket, and the Bedale, which was made for horseback riding. Either of these options in either classic navy or olive green will work for you within your preppy wardrobe. 

Quilted Jackets

Just like wax jackets, quilted jackets are a popular staple in a prep’s outerwear collection. To learn more about them, read out Quilted Jacket Guide.
 

Preppy Style Accessories 

Anchor Bracelets

Anchor bracelets are exactly what they sound like; bracelets that are made from a variety of fabrics and materials, usually rope, leather, or sail cloth, and fastened with a small metal or plastic anchor that operates similarly to a hook. 

This jewelry is very popular in prep culture both with men and women and is about as nautical as it gets. While you can find these patterns in solid blacks and grays, what’s most popular are the bright colors including blues, greens, and pinks. 

Belts

Colorful belts with motifs and stripes are an integral part of a preppy wardrobe. Often combined with brown leather and a brass buckle, these more or less flexible cloth belts are combined with chinos, Madras, or seersucker pants to create a bold look. 

D-ring or Ribbon Belts

Traditionally called a “Ribbon Belt,” D-ring belts have been around since the mid-1960s when introduced by J.Press. They provide a casual and fun flair to a normally conservative look. Some say that in order to wear them you either need a sense of humor or a small budget, since many D-ring belts are reversible offering two-in-one belts. 

There’s nothing exclusive or luxurious about ribbon belts. They’re just a lot of fun with various patterns. From the iconic tri-stripe belts and the five-stripe versions from Ralph Lauren to ones with embroidered lobsters and sail-boats lining them, the belts, although traditionally made of polyester, rayon, and nylon, now come in a variety of fabrics and materials from sailing cloth to fine cordovan leathers. 

Ties & Bowties

Although not exclusive to prep style, you’re bound to see more repp stripe neckties and bow ties as part of this aesthetic. Bold striped neckwear, resembling the collegiate stripes and crests, is a must here, but you can also focus on more professorial selections, including warm colors and small patterns, for a quieter take on preppy neckwear. 

Even More Preppy Style Essentials 

Madras

Madras is also a cotton fabric that is generally very lightweight and features a textured plaid design. In addition to pants, you can also find many pairs of shorts and jackets made of it. The Madras pattern is available in regular cotton and seersucker as well as patchwork madras, consisting of several different pieces of Madras cloth being sewn together. This is very popular in the prep culture and something widely used by Brooks Brothers, among other fine haberdashers that focus on prep style. 

Seersucker

Seersucker is another iconic fabric used in prep style. As a thin, cotton fabric that’s usually striped or checkered, it’s predominantly used to make summer clothing such as suits, shorts, pants, and other men’s and women’s clothing. Originating from India, the word seersucker literally translates to rice pudding and sugar which is pretty well what it resembles. Because of the way it’s woven, the threads often bunch together which gives it a wrinkled appearance. 

It’s because of this bunching that the fabric sits away from the skin when it’s worn which helps to keep the body cool, since it enhances circulation and dissipation of the heat. In other words, it’s fantastic to wear in the hot summer months – especially if you need to wear suits at work. 

Sporting Leisurewear

This particular area is quite vast, from cricket sweaters and vests to rugby shirts and shorts, virtually any item of clothing you see being worn at a predominantly preppy sport can be considered an integral part of prep culture and fashion. Think of classic leisurewear from activities such as golf, tennis, cricket, rugby, sailing, and equestrian apparel.

Tweed

During fall and winter, a true prep can rarely be seen without any form of tweed. Certainly a sure fire way to enliven a preppy outfit in cooler months, tweed in any capacity is a welcome addition to a prep’s wardrobe. 

Instantly Discover Your Perfect Colors

WhatColors helps you find what colors to wear based on your skin tone. Finally, our patented color match technology lets you get your season based on your skin tone. Get the perfect colors based on your season. Avoid colors that are a definite no. Based on your skin, eye, and hair color, find the perfect nail colors with our WhatColors Nail Color Generator. 

Get your color analysis done within 60 seconds with WhatColors’ AI personal color analysis app. Download our app for free today on the App Store or Google Play store.

7 Modern Women's Preppy Style Tips And 14 Ways to Implement Them Into Your Look

Preppy style is back and better than ever! The trend is characterized by its intelligent, classic, and tidy aesthetic. The preppy look is all about looking polished and put together, even if you are just grabbing brunch or running errands. One of the elements that makes the style so appealing is its versatility. You can mix and match preppy pieces for any occasion, from the office to a weekend getaway, or even a formal event.  The modern preppy look is also easy to personalize, allowing you to showcase your unique style and preferences. 

1. Blouses Are a Preppy Girl's Best Friend

No matter the season, a preppy outfit will always include a blouse. In fact, the more blouses, the better! The blouses that fit the preppy description are usually feminine, delicate, and lightweight. You can find them in:

• Long- and short-sleeve

• Patterned and plain

• Colorful and subdued, etc.
  
  

Essentially, you can always find a way to fit a blouse into your outfit. Some classic silhouettes include a collared blouse underneath a sweater, a feminine blouse with a pussy-bow tied in the front, flowing blouses with ruffled sleeves, and more. For example, pair a long-sleeve blouse with a pair for blue jeans for a summery casual look. Or, combine a crisp and clean white sleeveless blouse like this one with a pencil skirt for a look perfect for a day in the office. 

2. Sweaters Galore

Another cornerstone of the preppy aesthetic is the timeless sweater. Prepsters welcome this workhorse wonder in any iteration, from sweater vests to grandpa cardigans and the polished pullover. You’ll find all of these styles in any classic closet. Wondering how to wear a sweater vest in true women’s preppy style? 

Try one over a simple Oxford button-down shirt and pair with slim-fit ankle chinos. For another option, a dainty floral or women’s golf-inspired skirt will let the sunshine on your legs during the warmer months. Pair one with a matching cardigan set and add chunky-soled Mary Jane shoes. Harness your inner Cher Horowitz from “Clueless” and don knee-high socks. We are totally buggin’ over your perfectly put-together preppy outfit. 

3. Shoe Options to Complete the Look

Preppy shoes are usually simple, but they complete your look and make you feel like you're power-walking wherever you go. While any shoe style can work with a preppy outfit (except combat boots, perhaps), the following should be your go-to shoes in your perfect prep world. 

Mary Jane Heels

Names after the shoes worn by a comic book character in the early 1900s, these patent leather heels have also been seen on the runway for famous preppy brands like Dior and Yves Saint Laurent. The great thing about Mary Janes is that they are versatile and comfortable so you can pair them with jeans, a sheath dress, a blazer/slacks combo, and more. 

Ballet Flats 

Ballet flats are another must have that effortlessly go with almost all preppy outfits. They usually come in basic colors like navy blue, black, and white, but you can also find nudes, bright colors for a pop, and preppy patterns like plaid and polka dots. 

Loafers and Oxfords

For British boarding school and preppy student vibes, go for loafers or oxfords. These are great work options and pair well with slacks, skits, and even jeans. 

Boat Shoes

Would this be a preppy list without mentioning boat shoes? We think not. Turn a regular outfit into a preppy one by throwing on a classic pair of Sperries. Men can pull off boat shoes for fancier outfits, but most girly outfits with boat shoes are more casual in nature. Pair them with white jeans and a blue and white striped button up for an outfit that has you ready for a day out on the sailboat or at the country club. Boat shoes are also a perfect summer shoe that goes well with shorts and skirts. 

4. Preppy Style Patterns

While white, black, navy, and nude are the most common colors for preppy clothing, patterns play a key role in preppy outfits. Stripes, polka dots, plaid, and florals are all common patterns seen on tops, pants, skirts, and accessories. Look for dresses with all-over patterns to go bold with your patterned style. Or, combine a patterned cardigan, blouse, or accessory with mostly plain and clean colors to create the perfect balance. 

5. Color Options for Preppy Style

We mentioned the four main colors of prep style in tip #3, but don't let that limit you. Bright colored pants like yellow, pink, white, and red are all common in girl's prep outfits. You'll also find that many famous prep brands like Lilly Pulitzer use bright neon pinks, greens, yellows and blues in many of their clothes and accessories. Pastels are common in preppy style as well: pinks, yellows, greens, and blues especially.

6. Accessories Make the Outfit

Speaking of accessories, preppy outfits aren't complete until you throw on at least one or two accessories. For jewelry, you can't go wrong with pearls. Pearl necklaces and earrings can work for business and casual prep outfits. Spice up a basic outfit with a large statement necklace made of gold or silver. 

Headbands and hats are another common prep accessory for women. Skinny black headbands work with almost every outfit, but take a bit of a risk with a larger band, headbands with pearls/jewels attached, or bright color headbands. Bad hair day? Try a classic Black Dog or Vineyard Vines hat in pastels like blue, pink, and yellow. Tights, dainty wristwatches, and light scarves are other common accessories. 

7. Look for Inspiration in These Preppy Icons

We saved the best tip for last: look to and emulate your favorite preppy icons. These women are considered prep icons for a reason, so why not take the chance to style yourself after them? 

Jackie Kennedy 

Jackie Kennedy is perhaps the most famous prep icon to ever throw on pearls, sharp blazers, and all-white Cape Cod summer outfits. She embodies everything preppy girls strive to be. So take a look at some of her most iconic outfits and see what you can do to modernize them. 

Blair Waldorf 

Blair Waldorf is the famous prep from the hit show Gossip Girl. She successfully took Jackie's famous classic preppy look and made it modern. She wore tights, blazers, white gloves, sharp button-ups, pumps, pearls, etc. Watching even a couple of episodes of the show will give you outfit ideas that could style you for the next month. 

Emma Watson 

Emma Watson might not be as traditionally preppy as Jackie and Blair Waldorf, but she definitely embodies the modern preppy look. Collared shirts, sheath dresses, and simple color schemes define her style. She's also one of the faces of Burberry, which should clue you into her modern prep style.

How to Create the Iconic Looks

1. Mini Skirt with Blazer and Loafers

Matching a mini skirt with proper footwear to create a perfectly preppy style takes skill and consideration. In this case, the loafers complete the look ideally. A plated skirt accentuates the figure without any unwanted notes. Whether you head for the study, office, or lunch out, the look will seem perfect in place.

2. French Preppy with a Beret

We’ve all heard about the timeless Parisian charm, but many don’t know what it may look like. Well, a light blouse and a flowing skirt matched with a trendy beret is precisely the style you may want to replicate.

Styling tip: you can master the ‘French girl” vibe even if you don’t have a beret at hand. All it takes is a suitable cape, fedora, or cloche.

3. Black Mini Dress with Accented Collar

Preppy style takes the notion of a little black dress to a whole new level. It is pretty reserved but not over the top. A white collar is an ideal accessory that accentuates your sense of style.

Styling tip: use a detachable collar to rock the look. Besides, you can easily incorporate the item into a variety of other preppy-style outfits.

4. Preppy Look with Bicycle Shorts

Did you know that your fave bicycle shorts can become a key element in your preppy look? Well, all it takes is to throw in a classy white jacket with a comfy T-shirt to the mix, and you’ll succeed with a chic and modern assembly. Look at Loulou De Saison before a fashion show during Paris Fashion Week 2019 to move in the right direction.

5. Barbie Preppy Look

The Barbie fever isn’t over yet. That is why this Candela Pelizza outside Chanel Fashion Show 2019/2020 preppy look is a worthy idea to replicate. Don’t forget to accessorize the outfit properly – oversized earrings or a chunky necklace will complete the look ideally.

6. Tweed Green Suit with High Boots

Aimee Song was spotted after a fashion show during Paris Fashion Week 2019 wearing a chic and sophisticated combo of a tweed green suit and high boots you can wear in your everyday life. The ensemble vibrates with confidence and taste.

7. Preppy Look with a Long Cape

A long cape goes well with tailored blouses and high-waisted skirts. To add an extra spice to the look, choose a pair of boots that serve as a separate statement.

8. Bright Red Accented Suit

Red is a bold choice, no matter the style or occasion. Caroline Daur, seen outside the Thom Browne show during Paris Fashion Week Spring/Summer 2019, knew the drill and used it to her ultimate benefit. The fiery red suit paired with contrasting black accents projects sophistication and a creative attitude.

9. Tweed Mini Dress with a White Shirt

Tweed dress is a universal choice that elegant ladies usually make. However, a tweed mini dress leaves room for experimentation and personalization. You can pair a classy dress with a tasteful blouse to preserve the preppy flair, but your footwear will reflect your individuality and style.

10. Tweed Costume

A tweed costume is yet another timeless choice that practical and fashionable ladies prefer. Yet, it takes as much as a colorful pattern to take the look to another level of trendy and fun. Besides, you can always mix and match two different costumes, wearing the top from one and the bottom from the other.

11. Plaid Blazer with Accented OTK Boots

One may say that there’s no room for over the knee boots in preppy style. We beg to differ. A plaid blazer and accented OTK boots work in perfect tandem with one another. Don’t trust us? See for yourself!

12. Total Black Outfits

Black is an elegant color, and you can use it to succeed in a perfect preppy style as much as you want. In fact, a total black outfit is the ultimate ensemble suitable for workdays as well as evenings out.

13. Yellow Accents Preppy Outfits

There’s nothing wrong with making your preppy style a little brighter. An accent here, a pop of color there – and you will achieve a stylish combo that exudes energy and sass.

14. Houndstooth Print Tweed Suit with A Headband

A houndstooth tweed jacket is a modern take on the classy look. Pair it with a matching headband to spread a sophisticated yet playful vibe everywhere you go.

15 Must-Have Items for a Preppy, Girly, and Sophisticated Back-To-School Wardrobe

1. Girly Blouses

Look for feminine blouses that are roomy enough to not split apart at your chest but not so loose that they’re difficult to tuck into skirts and pants. Also, pay attention to how translucent your blouse is; a sheer blouse is a great piece, but only when you’ve prepared with the right undergarments!


Pro Tips: 

• Tuck a girly blouse into a pencil skirt for a great outfit that can easily transition from day to night. 

• Finish with a masculine watch and Mary Jane heels. 

• Feminine blouses even ruffled or pussy-bow variations, look fantastic under blazers for a business-casual sort of look.

• Accessorize with pearl earrings. 

• For the most versatility, look for shirts that align their buttons. That way, you can button it up for professional occasions and unbutton it for fun outings. 

• Blouses from Express are known for cutting their shirts perfectly for this!
  
  

2. Tights

Although you can definitely load up on inexpensive pairs of tights, I recommend getting at least one mid-priced name-brand or department-store pair. Nothing cheapens the look of an outfit quite like a pair of snarled, pilled, or awkwardly see-through tights!


Pro Tips: 

• A quality pair of tights will give your legs some excellent support, which is handy when paired with a lightweight dress. 

• Wear a colored pair of opaque tights with an A-line little black dress layered over a button-up dress shirt. 

• Finish with a pair of knee-high riding boots and a long statement necklace. 

• Don’t be afraid to wear colored opaque tights with an equally colorful dress or skirt! It’ll give you a girly yet mod look. 

• Finish the outfit with a pair of Mary Jane pumps.
  
  

3. Blazers

Blair Waldorf made her stuffy school uniform blazer look chic by pairing it with feminine extras, like scarves and her signature headbands. Blazers are also preppy-style must-haves—no negotiation! Start with a black, navy, or gray blazer, but branch out to other colors soon after!


Pro Tips: 

• Don’t have the cash for a proper business suit but have an important professional function coming up? Wear a fake one with a black blazer and black pants or a black pencil skirt. 

• Blazers look fantastic over sheath dresses. 

• Complete the look with a printed scarf, a watch, and pearl stud earrings. 

• For a fast and chic outfit formula, pair a chambray shirt with colored pants and add a blazer. 

• Finish with knee-high boots, a long statement necklace and a headband.
  
  

4. Thin Sweaters

Thin, crisp sweaters — especially those with cute graphics you’d find at J.Crew — are a great alternative to girly blouses during chilly fall and winter. I prefer to hand wash and air dry mine to preserve their perfect shape and softness.


Pro Tips: 

• Pair one with colored skinny jeans, ballet flats, and a headband. 

• A thin, solid-colored sweater will look retro fab with a skirt of your choice. 

• Finish the look with a statement necklace and heels. 

• Thin sweaters are perfect layering pieces. 

• Layer a button-down white or chambray shirt with the collar and cuffs folded out over a sweater.
  
  

5. Girly Headbands

Nothing pulls an outfit together quite as quickly as a well-placed headband. The great news is that they’re inexpensive and available everywhere, so you’ll never run out of options.


Pro Tips: 

• Throw a headband on with a ponytail to mask greasy roots. 

• Bow headbands are bold but look adorable when styled correctly. The key is to pair them with fewer other “cutesy” items.

• Include a few more androgynous pieces like a chunky watch or Oxford shoes to help balance them out. 

• Poof the crown and back of your head and spritz with hairspray before wearing a headband for a glamorous and luxurious look. 
  
  

6. Mary Jane Heels

Regular pumps are great, but Mary Jane heels will give you a preppy, girly vibe necessary when recreating this style aesthetic. As a bonus, they are much more comfortable than regular heels since they fit around your ankle so well.


Pro Tips: 

• Love height but have tender feet? Go ahead and buy a wedge Mary Jane — it’s better to be comfortable and do something unique than stick with a trend that makes your feet ache. 

• For a polished and sweet ensemble inspired by Emma Pillsbury, try a brightly colored sheath dress with a patterned cardigan. 

• Finish with a matching pair of Mary Jane heels, a pearl necklace, and a structured purse.

• Mary Janes looks great with skinny jeans and a fun party top. 

• Curl your hair with a large-barrel curling iron, and finish with shimmery make-up and a fancy headband.
  
  

7. Pearl Jewelry

An absolute staple of any preppy and sophisticated wardrobe is a classic set of pearl jewelry. Real pearls are expensive, but awesome lookalikes can be found almost everywhere. Look for pieces that have a substantial weight and aren’t too iridescent in color.


Pro Tips: 

• Pearl stud earrings make any outfi, even scrubby jeans and a t-shirt that looks polished and intentional. 

• A pearl brooch pinned to the lapel of a blazer or used to hold a scarf in place will look unexpected. 

• A long string of pearls around your neck will give you that preppy style and look fantastic with any LBD or sheath dress. 
  
  

8. Sheath Dresses

A perfect Jackie O-inspired sheath dress will carry you through interviews, nice lunches and dinners, business casual functions, hot dates, and much more. It’s a preppy-style must-have. The key to keeping this piece from looking boring or stuffy is to freshen it up with well-placed accessories.


Pro Tips: 

• Sheath dresses are ideal for formal occasions because they’re thick and structured. 

• Pair one with Mary Jane heels, a long necklace, and an easy updo for a great date night look. 

• Don’t be afraid of patterned sheath dresses! You can always tone it down with a blazer or a solid-colored cardigan. 

• They will also look mod and fabulous with opaque-colored tights.

• Look for styles that hit right at or slightly above your knees. They’ll be conservative enough for proper functions but short enough to play.
  
  

9. Statement Necklaces

I’m always amazed at how much a little jewelry can do for an outfit. A statement necklace is one of my preppy outfit ideas and fashion must-haves. It’s perfect for breathing life and glamour into basic tops.


Pro Tips: 

• Wear one with a thin sweater, a chambray shirt, a sheath dress, an open blazer

• Wear a long necklace with an infinity scarf or a triangle-shaped patterned scarf. The necklace and scarf should be two distinctive lengths so that you can see both. 

• Nautical-inspired chain necklaces are perfectly preppy and will look great with a blazer, a striped shirt, khaki chinos, and ballet flats.
  
  

10. Fantastic Skirts

Whether you prefer A-line, skater, or pencil-style skirts, these babies are essential in our preppy outfit ideas for crafting a sophisticated Blair Waldorf-inspired wardrobe. Get a mix of solid and patterned styles for maximum versatility.


Pro Tips: 

• Pair a skirt with a matching cami and cardigan combo and a pair of ballet flats for an outfit perfect for school. 

• Blair Waldorf rarely wore a skirt without a pair of opaque tights. 

• To remix this look, wear with a pair of ankle boots and a military jacket. 

• Never underestimate the feminine look of a girly button-down blouse tucked into a skirt. Finish with knee-high socks, a headband, and Mary Jane heels.
  
  

11. Ballet Flats

Ballet flats are a great addition to our preppy outfit ideas. They are the building blocks of many outfits, but they’re especially important for preppy and sophisticated wardrobes because of how feminine yet versatile they are.


Pro Tips: 

• I prefer inexpensive flats from places like Target and Gap. Flats are thin-soled shoes, so they’ll wear out fast regardless of which brand you choose. 

• Speaking of which, Tory Burch flats are a forever favorite. I loved the first pair I owned—they were black, quilted, and didn’t have elastic at the heel. They were so comfortable that I wore them almost every day! 

• Be sure you want a pair before making this big investment! If you lean more toward the preppy side and less toward the girly side, swap this piece out for penny loafers.
  
  

12. A Fabulous Coat

One of Blair’s signatures was her expensive-looking, glamorous coat collection. We might not all be able to afford dozens of coats from Barneys, but we can all at least have one special coat in our closet!


Pro Tips: 

• Since the cut is bold enough on its own, look for solid-colored styles for more versatility. 

• Pea coats in bold colors are a must for nailing the preppy style. They go with dresses, skirts, pants, leggings, and more! I also love patterned pea coats, tweed versions, and faux fur-trimmed styles. 

• A great winter coat is key to looking polished on frigid, windy days. You could wear three grubby sweaters and elastic sweatpants, but a great jacket and a pair of riding boots layered over them will instantly make you look chic.
  
  

13. Patterned Cardigans

Cardigans, especially the über soft variety, feel luxurious, sophisticated, and oh-so prim. A patterned one will help you bring some girly and fun style into an otherwise dressy and proper wardrobe.


Pro Tips: 

• Sweater sets aren’t just for old ladies anymore. Wear a matching top and cardigan set with a skirt, ballet flats and a statement necklace. 

• Cardigans look fantastic with girly ruffled blouses peaking through. 

• Try one with a lace cami and a pencil skirt! Forever 21 sometimes has thick cardigans, ribbon lining, and jeweled buttons that look almost Chanel-like. If you come across one of these, get on it! You’ll be happy you did.
  
  

14. Colored Pants

From skinny jeans to chinos, colored pants are an essential key to mastering preppy style. J.Crew is fantastic for colored pants that look sophisticated, rather than urban or über-trendy.


Pro Tips: 

• Cuff your skinny pants like a pro! Fold the hem of your pants no thicker than an inch, and fold over again. For the next (and last) fold, only roll the outer edge up, so the half on the inside of my leg is about an inch longer than the outside. This will elongate your legs, and make you look like you walked straight out of a photo shoot.

• Velvet and corduroy slim-cut pants are unexpected, but look fantastically polished with a girly blouse and a blazer. 

• Cuff your pants, and finish with oxford shoes and a menswear timepiece. 

• For a fast and easy outfit, throw on a thin sweater with a scarf, a headband, and knee-high riding boots.
  
  

15. A Skinny Belt

More often than not, the difference between making an outfit go from okay to wow is by cinching the waist with a skinny belt. They’re more subtle than thick belts, so they won’t take away from the other elements of your ensemble. Plus, they’ll give you shape and look totally flattering!


Pro Tips: 

• A sheath dress and cardigan combo will look polished and chic with a skinny belt around your waist. 

• For a cool look inspired by a J.Crew catalog, buy a belt a size too big and loop the tail around the band so the tail is faced down in an artful knot. 

• Juxtapose wide-leg trouser chinos with a girly ruffled blouse, and pull it together with a skinny belt at your hips.
  
  

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Related Reading

• Preppy Things
• Preppy Hairstyles
• Preppy Pics
• Preppy Shoes
• Preppy Girls
• Preppy Room Decor
• Preppy Shirts
• Preppy Profile Pictures
• Preppy Brands
• Preppy Makeup
• Preppy Images
• Preppy Sweatshirts
• Preppy Outfit Ideas
• How to Be Preppy
• Preppy Dresses

Do Preppy Girls Wear Jeans?

Absolutely! While jeans may not be traditional for preppy style, they can be styled in a preppy way. It’s all about balancing classic elements with your favorite jeans to create a polished outfit. I like to think of this as the modern approach to preppy style. 

Go Classic With a White Button Down

It doesn’t get easier than a white button-down with jeans. Try something slightly oversized, like the Sézane Max shirt, tucked into straight-leg jeans. Button-down shirts are a great staple for preppy style, either in classic white or a simple stripe. You can also throw a classic cardigan over your shoulders for the ultimate preppy outfit.

Roll up the sleeves and undo a few top buttons for effortless style. Pair a white button-down and jeans with classic accessories like a leather tote and loafers. A straw bag and ballet flats would also look really chic. Go simple with jewelry like pearl studs or a simple statement necklace like the Dorsey Moss.

Stripes Are a Must in Preppy Style

Is there anything more chic than a striped sweater and white jeans? It’s simple, classic, and timeless. To me, stripes are an integral component of preppy style. It’s also such an easy combination to create. The possibilities are pretty endless when it comes to picking a striped sweater—something with stripes of equal thickness or a skinny stripe. Color combinations like cream and navy, black and white, or camel and white all look great with white jeans.

For footwear, keep it simple with a strappy leather sandal, loafer, or ballet flat. You can elevate the look with classic gold jewelry, a pearl necklace, or a white sapphire necklace like the Dorsey Moss (I wear this one all the time). A simple leather crossbody or straw tote is the perfect accessory. 

Elevate Your Look With a Blazer

Pair a navy blazer with straight-leg jeans for a Ralph Lauren-style preppy outfit. There are plenty of ways to style a blazer with jeans, whether you do a basic tee, simple stripes, or white button-down. You can tailor it to the occasion, depending on if it’s casual or you’re headed to work.

Keep it simple with tan loafers, though you could also wear white sneakers. Accessorize with tortoise sunglasses and a straw tote.

Go for Luxe With a Sweater Set

This cashmere/silk sweater set from Kilte Collection is a dream. It’s luxurious, soft, chic and gorgeous. Made with mother of pearl buttons and a lightweight ribbed stitching it’s warm without being heavy or too hot and instantly elevates any outfit. Admittedly I’ve worn this on date night too many times to count but I just keep going back because I feel so good in it.

Pair a sweater set with with jeans and loafers for a night out or special occasion. You could also do a kitten heel or a strappy sandal for different shoe options. Add a cute leather bag and some simple jewelry. The Adelaide Engravable Heart Pendant Necklace is such a pretty everyday piece.

Preppy Style Isn’t Complete Without a Sweater Vest

Sweater vests are an iconic preppy fashion staple. They’re also really great for those in between seasons like fall and spring, when the weather changes drastically throughout the day. Sweater vests look great over a stripe tee or blouse with jeans. Leather sandals, ballet flats or even clogs look timeless and chic. Accessorize with a straw or leather tote. 

Stay Warm in a Chic Knit Sweater  

For winter weather, a stylish knit sweater over a button-down shirt with wide-leg jeans will keep you warm and chic. A wool robe coat to pull the look together is always timeless. See how to wear wide-leg jeans here.

For spring, these jeans cuffed with sandals or a loafer would look really chic with a lighter knit or white button down shirt.

43 Preppy Clothing Brands That Will Elevate Your Wardrobe

1. J.Crew

 All the preppy girls like to shop at J.Crew. It’s also one of our favorite preppy brands here at MCO for a good reason! This classic brand has a wide selection of timeless clothes. You can find everything from tweed dresses and button-down linen dresses to shirt dresses that are fit for tea parties and soirées. 

J.Crew also has no shortage of crisp white button-down shirts that embody a chic spirit. This famous preppy brand will also be your go-to shop for:

• Blazers

• Dress pants

• Cashmere sweaters and more
  
  

Price range: $20 – $1,251  

2. Tommy Hilfiger

Get ready to fall head over heels in love with the preppy pieces from Tommy Hilfiger. This legendary brand has been great at crafting iconic preppy college American styles since 1985. Tommy Hilfiger offers elevated and sophisticated pieces with a playful and modern twist. So, if you’re looking for preppy clothes with a contemporary flair, Tommy Hilfiger is calling your name. 

You can find great American classics with a Tommy twist, like slim-fit polo shirts that boast the iconic TH logo. The brand also has polo dresses that would be great for rocking at country clubs. Other timeless and charming clothing items include relaxed straight-leg pants, oversized striped cardigans, khaki trench coats, leather mid-block heels, Oxford shirts – the list goes on. 

Price range: $25 – $300  

3. Abercrombie & Fitch

Create the perfect preppy uniform with clothes from Abercrombie & Fitch. The history of Abercrombie dates back to 1892 when David Abercrombie, an outdoor specialty retailer, founded the brand. The Abercrombie company later became Abercrombie & Fitch in 1904 when Ezra Fitch joined the brand. 

Since then, Abercrombie & Fitch has been making clothes with an optimistic American spirit. If you’re looking for comfortable and classy dresses, Abercrombie & Fitch has premium linen midi dresses and poplin dresses. You will also love the tailored pants, polished polos, oversized poplin shirts, and plenty more elegant pieces. 

Price range: $19 – $220 

4. Tory Burch

Adding pieces from Tory Buch will not be a decision you will regret. The brand was founded by American fashion designer Tory Burch in 2004. This New York-based brand is well-renowned for its irresistibly chic handbag collections. Some must-have handbags you need in your preppy closet are the Perry compartment tote bags and the Robinson top handle bags. 

These timeless bags will look great with all your preppy outfits. On top of the luxurious bags, Tory Burch has ready-to-wear pieces that are effortlessly polished. You will find everything from belted coats, poplin shirt dresses, collared crewnecks, smocked dresses, and tailored pants, to many more incredible pieces. 

Price range: $49 – $2,398

5. Kate Spade

Kate Spade is an excellent place to explore for preppy and pretty clothing. The brand was founded by Kate and Andy Spade in 1993 to offer high-end bags at an affordable price point. Since its inception, Kate Spade has focused on providing pieces with an optimistic and feminine spirit. You will see floral crossbody bags, tote bags, and elegant clutches. Besides the amazing bag collection, Kate Spade offers other cute and classy accessories. This includes:

• Floral print silk scarves

• Oval sunglasses

• Polka dot umbrellas, and more
  
  

Kate Spade is also the place to look for polished and feminine clothing. You can find everything from stripe wrap dresses to floral one-shoulder dresses, and spring gingham pants. 

Price range: $48 – $800  

6. Lilly Pulitzer

Lilly Pulitzer should be your go-to brand for timelessly chic preppy clothes. This iconic fashion brand blossomed after Palm Beach socialite Lilly Pulitzer started her juice stand in the 1950s. After a few lemonade spills on her dress, the late Lilly collaborated with a dressmaker to create spill-proof linen dresses with a cotton-lined design. And the result? The first Lilly shift dress was born. This dress caught the attention of fashion lovers in Palm Springs to the point where every fashionable woman wanted a dress. 

Lilly Pulitzer also gained more success after Jackie Kennedy was featured on the front cover of Life Magazine wearing a Lilly dress. Fast-forward to more than 50 years later, and Lilly Pulitzer is still a fan favorite among fashionistas who love clothes with a charming and timeless allure. The shift dresses are the bestsellers, but you will also fall in love with many more styles. This includes ruffle tops, relaxed button-down shirts, and fun accessories. Every piece is guaranteed to add some joy and femininity to your closet. 

Price range: $48 – $648  

7. Vineyard Vines

Vineyard Vines began in 1998 after two brothers, Shep and Ian Murray, grew tired of working at their office jobs. They set out the goal of exchanging their mundane office life for fun outdoor adventures. The brothers decided to share their love for the American dream and Martha’s Vineyard in their fashion brand (hence the name, Vineyard Vines). The brand is defined by the preppy ethos of the summer and the quintessential East Coast lifestyle. 

It also targets anyone trying to live the good life. Vineyard Vines’ collections include straw tote bags, cashmere cardigans, silk shirt dresses, and many more pieces that embody timeless elegance and coastal charm. Wear the clothing to seaside escapades, a Kentucky derby, or summer nuptials. 

Price range: $18 – $650  

8. Sperry

Sperry embodies a fun and elegant spirit and makes waves in the fashion industry with its iconic boat shoes. The brand was founded in 1935 when the founder, Paul Sperry, fell overboard from a boat. This accident inspired him to make the world’s first slip-resistant deck shoes to help him continue doing what he loved the most: sailing! 

Eventually, in 1946, new Sperry styles were launched, and they could be used beyond the sea for everyday usage like playing tennis and leisure. So if you’re hunting for preppy footwear, Sperry should be your go-to destination for the finest boat shoes. Boat shoes with floral motifs, leather materials, and mule finishes come in different styles, colors, and finishes. 

Price range: $50 – $199.95  

9. Lacoste

Have you ever wondered who was behind the idea of the shirts and clothes with the crocodile logo? The legendary Tennis champion René Lacoste invented the world’s first short-sleeved polo shirt in a breathable fabric to make playing tennis more comfortable. This shirt gave him a light-bulb moment to launch the brand Lacoste. He launched the brand with the principles of breaking fashion rules while keeping it classy and elegant. 

Inspired by his fearless skills on the court, Lacoste earned the playful nickname “the crocodile.” This nickname sparked the brilliant idea of making the crocodile his brand's logo. Now the iconic crocodile is synonymous with effortless elegance and athletic chic style. Lacoste has all the elegant clothing items and must-haves to meet your preppy fashion needs. You will find everything from:

• Timeless sweater vests

• Monogram varsity jackets

• Polo shirts

• Tapered checkered pants

• Canvas tote bags
  
  

Price range: $15 – $800  

10. Talbots

Talbots is the type of preppy clothing brand that you will never stop once you start shopping there. This women’s brand was founded in 1947 by Nancy and Rudy Talbot, emphasizing modern, classy, and smile-worthy clothes for every occasion. Talbots are brimming with the best preppy clothes, from polished casual pieces like:

• Linen blazers

• Tweed collarless jackets

• V-neck sweaters

• Great fancy dresses
  
  

Price range: $11 – $428  

11. Southern Tide

Southern Tide is for the fashion-forward woman who loves a preppy and southern style. The brand was founded in 2006 in South Carolina. The first product to get them on the fashion map was their Skipjack polos. The polos became a hit in fashion because of their fit, design, and comfort. The brand later added clothing collections that were not just for tennis matches and other outdoor adventures but for many other occasions. 

So, whether you have a fancy dinner date or want to go on a casual outing, Southern Tide has a great selection of high-quality and timeless coastal pieces. Think stripe dresses, wide-leg pants, twill shorts, and crewneck t-shirts. What’s also great about Southern Tide is its special collegiate collection, so you will have endless access to the best polo shirts, button-down shirts, and much more. 

Price range: $58 – $200  

12. Brooks Brothers

Brooks Brothers is the epitome of preppy style. The brand was founded in 1818 to design classic American styles. It has been a fan favorite among 39 American presidents and dapper Ivy League gentlemen. 

The brand isn’t only a men’s brand; Brooks Brothers has expanded its offering to women. The legendary brand offers clothes that fall under the preppy style. You will find everything from chic suit separates to linen dresses, polished polos, and more. 

Price range: $42 – $600 

13. Rowing Blazers

If there is one preppy brand you need to have on your radar, it’s Rowing Blazers. Jack Carlson, who was on the U.S. national rowing team, established the brand. Rowing Blazers offers classic blazers with a modern take, bright colors and unique touches. 

So, if you’re searching for preppy blazers with streetwear and sporty influences, Rowing Blazers is your brand. Beyond the blazers, this brand also has a great selection of polo t-shirts, knits, and leisurewear. 

Price range: $18 – $800

14. Alice + Olivia

Alice + Olivia was born from Stacey Benet’s love for vintage and feminine styles. This A-list favorite brand has a great selection of whimsical yet classy designs to complete your preppy wardrobe. Some bestseller items are:

• Denim dresses

• Wide-leg pants

• Midi dresses
  
  

Price range: $50 – $1,000  

15. Land’s End

In 1963, Land’s End was built on the principles of crafting high-quality clothing pieces for the entire family. The brand combines elegance and functional designs to create timeless, comfortable pieces. 

The goal is to make their clothes so soft and easy to wear that they feel like you are experiencing Sunday comfort daily. With the endless selection of blazers, coats, fleece tops, chino pants, and more, you can easily put together the best preppy looks! 

Price range: $34.95 – $500  

16. Sporty & Rich

Want to look like a sporty and rich Ivy League student? You need to check out this timeless brand. It was established from a dreamy mood board about life’s beautiful moments, mixing past inspirations with modern elegance. The brand evolved from a chic print magazine to a preppy fashion brand that offers simple yet elegant styles that outlast the fashion calendar. 

Price range: $40 – $345  

17. Wilfred

Wilfred is an exclusive brand by the iconic fashion label Aritzia. What we love about Wilfred is the endless option of feminine and flattering pieces. The pants have a chic appeal, the trench coats are timeless, and the tops exude a romantic flair. 

Price range: $8 – $378  

18. Barbour

John Barbour established his namesake label in 1894. His most popular design for the brand is the wax cotton jacket, which was launched in 1936. Due to its style and durability, it became a go-to jacket for motorcycle riders. The luxury English brand has other great pieces that are exceptionally made and will stand the test of time. Barbour has a good collection of:

• Cardigans

• Jackets

• Tailored pants

• Boots and more
  
  

Price range: $26 – $600  

19. Hunter Boots

You’ve probably seen the royals and Hollywood celebrities sport Hunter Boots. This popular brand has amazing boots that will go with any preppy outfit you can think of. They can accompany jeans and a button-down blazer, a flowy wrap dress, or even a trench coat and jeans – the endless styling possibilities. 

Price range: $60 – $700 

20. J.Mclaughlin

Immerse yourself in the stylish and preppy world of J. McLaughlin. This brand was launched in 1977 by two brothers, Jay and Kevin, to craft classic American sportswear apparel with a modern twist. J. Mclaughlin prioritizes timeless style over fleeting trends. 

Plus, the J brand is all about designing clothes that are not pretentious. You will not have a dull moment scrolling through the J. Mclaughlin website. The brand has fancy pieces in signature prints that are great for formal occasions and casual days, such as:

• Long sleeve tops

• Blazers

• Tailored shorts

• Polished accessories
  
  

Price range: $58 – $595  

21. Sail to Sable

In 2012, Jennifer Stocker traded her publishing career for a fashion venture. She started Sail to Sable out of a passion for classic silhouettes, statement prints, and dreamy summer adventures on the East Coast. Jennifer’s female-led brand curates resort wear that effortlessly elevates everyday style with a preppy, coastal charm. 

Price range: $148 – $300

22. Ted Baker

For effortless preppy woman style, head over to Ted Baker. The brand has many preppy and feminine pieces, including:

• Tote bags

• Romantic floral dresses

• Drape-neck tops

• Slingback pumps and more 
  
  

Price range: $35 – $700  

23. Banana Republic

Banana Republic has no shortage of preppy clothes to take your style from bland to preppy in seconds. Mel and Patricia Ziegler founded the brand in 1978 out of a spirit of adventure. You can find everything from:

• Blazers

• Trench coats

• Sweaters, and many more wardrobe classics 
  
  

Price range: $50 – $800  

24. Ralph Lauren

This preppy clothing brands list wouldn’t be complete without Ralph Lauren. For over 50 years, Ralph Lauren has designed clothes that tell a story of authenticity and timeless elegance. You will find polo shirts, jackets, and button-down shirts that blend sophistication with allure. 

Price: $22 – $1,000  

25. Michael Kors

Let’s discuss Michael Kors – the epitome of chic and accessible luxury. American fashion designer Michael Kors started his namesake brand in 1981. For over 40 years, Michael Kors has always delivered the most fashionable pieces, which is why this brand should be your go-to for polished accessories, garments, and more. 

Price: $155 – 1,295  

26. Levi Strauss & Co.

Every preppy wardrobe needs a stylish, classy, and reliable pair of jeans. After all, jeans are the building blocks of most preppy outfits, so Levis is a good brand to check out. Levis, a brand that has shaped fashion and popular culture, was founded in 1853 by Levis Strauss, an immigrant from Bavaria. 

Setting up shop in San Fransisco, California, during the California Gold Rush, he identified a need for durable workwear. This led to a collaboration with tailor Jacob Davis, resulting in the invention of the iconic ‘Blue Jeans’ in 1873. From being exclusively worn by gold miners, these jeans soon found favor with Hollywood starlets like Marilyn Monroe, marking the beginning of their iconic journey through popular culture. 

Price range: $50 – $128  

27. Coach

Level up your accessories with Coach. Lillian and Miles Cahn co-founded the iconic brand out of the inspiration of creative director Stuart Vevers, who wanted to make durable pretty things. 

Price range: $35 – $750 

28. Guess

Guess was founded by the Marciano brothers in 1981. They swapped their love for the South of France for the American dream. The brothers used their European influence to inject an elegant flair into denim. The result? The iconic Menlyn jeans were born. The brand has expanded beyond denim to dresses, handbags, and more. 

Price range: $25 – $500  

29. Nautica

Nautica is one of the best preppy clothing brands for warm weather style. It was founded in 1983 to design nautical-inspired clothes (hence the name). If you need preppy clothes for this summer, I recommend getting items from Nautica. 

Price range: $8 – $85  

30. Hugo Boss

Hugo Boss is not just a preppy brand for gentlemen, this German brand also has great pieces for women as well. You will not be disappointed with the wide selection of modern and classy pieces! 

Price range: $35 – $600 
 

31. Cole Haan

You might not have heard of Cole Haan, but when you see the timeless footwear the brand offers, you will definitely want to shop there. Cole Haan was established in 1928 to offer excellent craftsmanship, comfort, and design. For nearly a century, it has created shoes with a traditional American style and bold innovations. 

The brand has preppy footwear for formal occasions, casual outings, and more, including loafers, ballet flats, espadrille sandals, and Oxfords. You’re guaranteed to find polished shoes for your preppy wardrobe. 

Price range: $90 – $425  

32. Loewe

This Spanish luxury brand was founded in Madrid in 1846. Its tone is chic and classic, with influences from art. So, if you need luxurious items for your preppy closet, Loewe should be your one-stop shop for the perfect clothing. Loewe is a great place to discover the best styles, from its signature raffia tote bags to its iconic leather footwear. 

Price range: $300 – $3000

33. Mango

If Loewe is out of your budget, consider shopping at Mango. This Spanish brand has amazing classic pieces without the steep price tag of some designer brands. You will find everything from trench coats to sweaters, loafers, classic sunglasses, and more. 

Price range: $18 – $650  

34. River Island

Another brand to have on your fashion radar is River Island. This iconic British high-street brand was founded in 1959. It is inspired by heritage styles and modern influences. The brand offers classic silhouettes that will perfectly align with your preppy style. These include intelligent blazers, tailored pants, and button-down shirts. 

Price range: $10 – $200

35. Club Monaco

Since 1985, the Canadian brand Club Monaco has been focused on creating “better basics.” The brand is committed to creating effortlessly chic classics that will make your life easier. So, if you need to stock up on preppy basics, Club Monaco is calling your name. 

Price range: $32.50- $950 

36. Frank and Oak

Under-the-radar brand Frank and Oak was founded in 2012 to inspire better living by designing eco-conscious clothes. It’s a great brand to shop from if you’re looking for ethically made preppy clothes. Some of the most popular items from Frank and Oak are bermuda shorts, striped bubble cardigans, relaxed blazers, and straight-leg jeans. 

Price range: $10 – $600 

37. L.L.Bean

Need classic outdoor outfits? Look no further than L.L. Bean. Leon Leonwood Bean started this brand in 1912 to deliver exceptionally crafted and timeless outdoor clothes. The brand offers everything from insulated jackets to sweaters, sandals, jeans, and more.
 

Price range: $20 – $180 

38. Gap

You can always depend on Gap to give you the best wardrobe staples to build your preppy wardrobe. The brand was founded in 1959 with the goal of making the search for the perfect pair of jeans easier. More than 50 years later, Gap is not only the place to find a good pair of jeans; it’s also the go-to shop for:

• Classic white tees

• Sweaters

• Cardigans

• Shirts and more 
  
  

Price range: $18 – $230 

39. LOFT

Get ready to be obsessed with the modern and feminine pieces at LOFT. This brand has everything you need to create that effortless, preppy, and girly style. Loft offers:

• Spring tweed jackets

• Striped poplin dresses

• Rugby-collared sweaters, and many more charming clothes
  
  

Price range: $19- 180 

40. Draper James

If you’re a fan of Reese Witherspoon, you’re going to love her clothing line. Most celebrity clothing lines miss the mark, but Draper James actually has some lovely clothing pieces. Classic prints like florals and checkpoints are a prominent theme in Draper James’ collections, which is great if you’re looking for preppy clothes with a feminine touch. 

Price range: $43 – $300 

41. Dudley Stephens

Step up your style with Dudley Stephens, a women-led brand that caters to the modern woman’s preference for classic styles over fashion trends. Dudley Stephens is committed to sustainability, crafting pieces that stand the test of time in recycled performance fabrics. You will surely find a piece that speaks to your classic style from turtlenecks to pullovers, shorts, and more. 

Price range: $148 – $200

42. Hill House Home

Hill House Home should be the brand to explore for preppy clothes! The brand prides itself on celebrating life by offering exceptionally quality classic styles. Experience the elegance of Hill House Home, a brand that embodies the preppy vibe with its elegant yet simple designs. 

Picture yourself in their pretty puff sleeve dresses, a style that instantly transports you to the Hamptons. And don’t forget to check out their cool accessories, perfect for adding a touch of spice to your preppy outfits. 

Price range: $18 – $828 

43. Tuckernuck

The last preppy clothing brand to know is Tuckernuck. There is a lot to love about this fashion retailer. Tickernuck has the best brands that offer effortlessly fresh styles, such as classic ballet flats, raffia tote bags, flowy dresses, polo shirts, tweed dresses, and more. 

Price range: $24 – $1,000  

5 Ways to Dress Preppy on Any Budget

1. Prioritize Versatile Pieces

You must make every dollar count when building a preppy wardrobe on a budget. The fastest way to do that is to purchase versatile clothes. Look for clothes that lend themselves to the “preppy” look but also fit with just about anything else you’ll wear. Here are a few suggestions. Stretch twill pants. A pair of chinos like these sunny stretch compact twill pants in dusty silver can match with anything preppy like:

• Boat shoes

• Button-downs

• Polo shirts and more
  
  

Think of a good pair of twill pants as the foundation upon which to build the rest of a classic preppy outfit. And with a durable twill construction, you’ll be able to wear these pants over and over again—classic vintage twill. Stretch twill is great for performance, but if you want to lean more toward a “vintage preppy” look, classic vintage twill is your choice. Charleston brick vintage twill pants fit nicely into any preppy wardrobe and offer a stylish alternative to ordinary denim. Once again, the key here is purchasing a great pair of pants you can use any day of the week.

2. Mix and Match Your Layers

Dressing preppy is often associated with the careful application of layers—a sweater over a button-down, a navy blazer over two distinct layers in cooler weather. You can get more out of your clothes if you use your purchases to mix-and-match your layers regularly. How can you accomplish that? 

Here are some tips. 

• Use versatile colors. It’s not hard to mix and match when you’ve got colors like navy, white, khaki, and salmon in your wardrobe. 

• Stick to versatile colors with your limited budget. 

• Try “pops” of contrast. A colorful dress shirt under a monochromatic sweater can offer an outfit a nice “pop” of color. But don’t limit these pops to just colors. 

• Think about contrasting textures (smooth cotton vs. wool-knit, for example) to make your outfits more interesting.
  
  

3. Skip the Over-Priced Brands

There’s a stigma out there that anything preppy must also be expensive. But this isn’t necessarily the case. Dressing preppy is simply a style—it doesn’t require a dollar amount, and there’s no barrier to entry. 

Don’t fret about buying an item that might be on sale because of seasonal considerations. An item of clothing is still high-quality even if the price on it goes down. It doesn’t make you un-preppy to seek it out. It only makes you discerning and frugal. Go with a brand that offers prep-worthy clothes at the right prices. 

4. Don’t Try Too Hard When Going for Preppy Style

It’s easy to get enthusiastic about something you enjoy. But your newfound appreciation shouldn’t endanger you to potential ridicule. Most of us remember those memes of insufferable douchebags in salmon shorts and Brooks Brothers button-downs. It’s a short road to overselling the look, and earning the title of clown prince douchelord (if you haven’t already). 

5. Never Go Full Preppy Style

This ties in with caveat numero uno. Prep style is all about being effortless. There’s no need to incorporate everything at once. If you spend most of your time in Bintang singlets and trackies, your mates might ask what the story is if you rock up to knock-offs in boat shoes and a button-down, with a sweater around your shoulders. 

It takes a brave bloke to cop that roasting, so don’t go full retard. Stick to one or two pieces to start. Avoid imitating your American lacrosse mates head-to-toe, even if they look the business and score more chicks than you do.

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