As the leaves begin to change and the air turns crisp, we can all appreciate the return of cozy layers and rich autumnal tones. But, if you’re like me, you might have trouble saying goodbye to your summer wardrobe. Transitioning into preppy aesthetic can be tricky. Preppy clothes are a classic choice that can help you easily navigate this seasonal change. A few versatile pieces, like a cable-knit sweater or a pleated skirt, will elevate your style and pair nicely with your existing summer favorites. We’ll explore the charm of preppy clothes and how to incorporate them into your wardrobe for fall.  We’ll also share some insight on choosing the right colors to complement your style so you can feel confident in your look.  

WhatColors’ AI personal color analysis app can help elevate your style by providing personalized color recommendations based on your unique traits. These insights allow you to choose the right colors to curate your preppy wardrobe.

Table of Contents

• What Are Preppy Clothes & Where The Name Came From

• What Are the Preppy Colors, Fabrics, and Styles?

• 24 Preppy Clothing  Essentials for Men in 2024

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

• 11 Ways to Get the Preppy Look for Kids

• The 4 Hottest Preppy Trends in 2024

• 7 Essentials Defining Modern Preppy Style

• 20+ Chic and Classy Preppy Outfit Ideas for Women

• 4 Preppy Outfit Style Ideas for Guys

• 33+ Timeless Preppy Fashion Brands For Every Budget

• Try AI Personal Color Analysis For Free Today

What Are Preppy Clothes & Where The Name Came From

Preppy fashion has its roots in the early twentieth century when wealthy young men attended Ivy League schools and donned smart casual outfits that reflected their privileged upbringings. The term preppy and its variations like prep and prepster come from the word preparatory, as these elite institutions are often called prep schools. 

The look was a status symbol and included classic pieces like:

• Button-down shirts

• Knitted sweaters

• Loafers 
  
  

It has morphed into an aesthetic that is more accessible to a wider audience, and today, it’s not uncommon to see high school students sporting preppy looks.

Characteristics of Preppy Style

At its core, preppy style is all about classic, tailored pieces that are polished yet relaxed. The outfits often look as though they could be worn on a college campus or during a relaxed day at a wealthy summer resort. 

The color palettes can vary, but many outfits incorporate bright colors and cheerful prints that evoke a sense of nostalgia. Preppy style has also been known to include elements of athletic wear, especially pieces that are classic and timeless.

Key Moments In Preppy History

The preppy look became popular in the 1950s, thanks in part to film and television, which portrayed the lives of affluent teens leading comfortable, carefree lives. The style saw a resurgence in the 1980s with the publication of The Official Preppy Handbook, which humorously detailed the:

• Clothes

• Culture

• Vocabulary of preps
  
  

The style has continued to evolve, with trends in the 1990s, 2000s, and beyond that mix classic prep elements with other aesthetics.

What Are the Preppy Colors, Fabrics, and Styles?

A few key elements define the preppy look:

• Colors

• Materials

• Styles 
  
  

The right combination of these factors can achieve the perfect preppy look. Let's break it down. 

Picking the Right Color Palette for Preppy Outfits

The preppy style is characterized by its distinct color palette and patterns, such as:

• Blue

• Light blue

• Green

• Yellow

• White

• Black 
  
  

Are staples, often accented with pink, beige, and bright red. 

• Plaid

• Checks

• Stripes

• Tweed 
  
  

These are undoubtedly the main patterns seen within the aesthetic. They are classically used in tailored blazers paired with chinos or skirts in mini, midi, and maxi lengths. For a playful twist, polka dots and leopard-printed accessories like scarves and handbags are the best bet. Gingham checks, a favorite for spring and summer, grace sundresses and button-down shirts, infusing preppy fashion with a fresh, youthful vibe.

Choosing the Right Fabrics for Preppy Style

Preppy style should be a matter of style and choice of fabric. The preppy style is all about choosing the right fabrics like:

• Fine cotton

• Tweed

• Wool 
  
  

They are staples in any preppy wardrobe. Choose:

• Cotton shirts

• Skirts

• Dresses
  
  

You can also opt for a tweed jacket or skirt perfect for chilly autumn mornings.Wool is another great fabric to choose from. It adds a touch of sophistication and warmth to any preppy outfit. Investing in high-quality fabrics will ensure that your preppy wardrobe withstands the test of time and maintains its classic appeal.

Key Preppy Styles for Fall

A preppy aesthetic aims to achieve a polished, effortless look. You can achieve this by mixing and matching contrasting patterns and textures. Try pairing a striped shirt with a plaid skirt or adding a tweed blazer over tailored pants. 

Experiment with different textures and prints until you find the perfect combination. To complete the outfit, you can also experiment with layering different pieces to add depth. 

Balancing Classic and Modern Elements in Preppy Fashion

Wear a collared shirt underneath a sweater or add a statement belt to cinch your waist. The key is to balance classic and modern elements to create a preppy yet unique style. 

This style is all about simplicity and effortlessness. Avoid excessive accessories, overly complicated outfits, and anything too trendy or flashy. 

Timeless Pieces and Clean Lines for a Refined Look

Stick to classic pieces and clean lines for a timeless and refined look. Opt for neutral colors or timeless patterns like stripes and plaids. 

Your outfit should be understated yet sophisticated. Keep your hair and makeup natural and minimal to maintain the effortless preppy vibe.

Mastering Preppy Style: Embracing Classics and Quality

Achieving the preppy look is mastering the classics, finding the perfect fit, mixing and matching, and embracing classic patterns. Preppy fashion is all about understated elegance and quality pieces that stand the test of time. 

With these preppy fashion tips, you can easily create a wardrobe that will make you feel confident and stylish.

WhatColors helps you find what colors to wear based on your skin tone. Finally, get your season based on our skin tone, thanks to our patented color match technology. 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.

Related Reading

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• Preppy Room
• Preppy Stuff
• Preppy Nails
• Preppy Bedroom

24 Preppy Clothing  Essentials for Men in 2024

1. Classic Navy Blazer 

The classic navy blazer is perhaps the ultimate preppy jacket. A staple in collegiate style, the navy blazer can be worn with almost anything. Pair it with a button-up Oxford shirt and khaki chinos for a traditional look. 

You can also add a rep tie for good measure. Swap the chinos for flat-front shorts in a muted color to make the look more modern and ditch the tie. You can even go with a graphic tee instead of the button-up, and of course, accessorize with some boat shoes or loafers.

2. 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 sports 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.

3. 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:

• Collar

• Placket

• 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

• Various synthetic materials. 
  
  

These shirts are often worn with shorts or trousers but can also be paired with a blazer or sports jacket.

4. Chinos  

Chinos are trousers made from a twill fabric, originally made of 100% cotton. While they can be found in synthetic blends now, the best is still made of cotton. 

Brooks Brothers offers a superior selection, as do many other fine clothes. They come in many colors, but the most common is khaki, which is still very popular in coastal culture.

5. GTH (Go To Hell) Pants  

GTH pants take some serious getting used to. This is a style of its own 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

• 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. The winner is viewed as the most daring dresser around. Just use some caution when pairing them.

6. Nantucket Reds  

Nantucket Reds are an essential component of prep culture:

• Red pants

• Shorts

• Shirts

• Hats

• Other articles 
  
  

Originally distributed by Murray’s Toggery Shop in Nantucket and are guaranteed to fade to an almost rosy pink. They are traditionally pants, 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.

7. Argyle Sweaters  

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

The pattern can consist of diamonds or lozenges. Typically, they overlap in a motif, adding a sense of multiple dimensions and texture. It’s used as an overlay of intercrossing diagonal lines on solid diamonds.

8. Cable Knit Sweaters  

Cable-knit sweaters are classic and will never go out of style. Whether made of cotton, wool, or cashmere, with sleeves or without, they are a preppy wardrobe staple. 

A crew neck is the way to go if you wear bow ties, 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.

9. Rugby Shirts  

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

10. Tennis & Cricket Sweaters

Tennis or Cricket sweaters are a must-have in a preppy wardrobe. 

11. Boat Shoes  

Like many staples in prep style, you either love or hate boat shoes. While many credit Sperry Topsider with the initial introduction, and most people consider them the quintessential boat shoe, many companies today make them. 

Boat shoes are exactly what they sound like. They were created as non-slip shoes 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 casual shoes and are tied using leather boat shoelaces.

12. Loafers  

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

Loafers are casual shoes, 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 various:

• Styles

• Colors

• Materials

• Occasionally 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.

13. L.L. Bean Boots  

Founded in 1912 by Leon Leonwood Bean and was quickly known for its 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 company's annual sales are north of 1.5 billion. 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.

14. White Shoes  

White buckskin shoes, aka white bucks, are a popular preppy companion to seersucker pants, cocktail parties, horse races, or anything related to summer. Paired with:

• Linen

• Chinos

• Seersucker
  
  

They give the wearer a debonair, seasonally appropriate look. Buckskin leather is technically made from 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 also be very nice. Many white bucks come with a lightweight, red rubber sole, although they can also be found with classic leather soles in Goodyear's construction.

Preppy Outerwear: Don’t Forget a Warm Layer

15. Barbour Wax Jacket  

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

16. Quilted Jackets 

Just like wax jackets, quilted jackets are a popular staple in a prep’s outerwear collection.

Preppy Accessories: The Icing on the Cake

17. Anchor Bracelets  

Anchor bracelets are exactly what they sound like; bracelets are made from various 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 with men and women and is about as nautical as possible. 

You can find these patterns in solid blacks and grays and bright colors, including:

• Blues

• Greens

• Pinks 
  
  

They are the most popular.

18. Belts  

Colorful belts with motifs and stripes are integral to 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.

19. 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 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

• Nylon 
  
  

It comes in various fabrics and materials, from sailing cloth to fine cordovan leathers.

20. Ties & Bowties 

Although not exclusive to prep style, you’ll 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. Still, you can also focus on more professorial selections, including warm colors and small patterns, for a quieter take on preppy neckwear.

21. 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, which consists of several different pieces of Madras cloth sewn together. This is very popular in prep culture and is widely used by Brooks Brothers, among other fine haberdashers focusing on prep style.

22. Seersucker 

Seersucker is another iconic fabric used in prep style as:

• A Thin cloth

• Checkered fabric 
  
  

it’s predominantly used to make summer clothing such as:

• Suits

• Shorts

• Pants

• Other men’s and women’s clothing
  
  

Originating from India, the word seersucker translates to rice pudding and sugar, which is what it resembles. 

Because of how it’s woven, the threads often bunch together, giving it a wrinkled appearance. Because of this bunching, the fabric sits away from the skin when worn, which helps keep the body cool by enhancing circulation and dissipating heat. In other words, it’s fantastic to wear in the hot summer months—especially if you need to wear suits at work.

23. Sporting Leisurewear  

This area is vast; from cricket sweaters and vests to rugby shirts and shorts, virtually any item of clothing you see being worn at a predominantly prep 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

• Equestrian apparel
  
  

24. Tweed  

A true prep can rarely be seen without tweed during fall and winter. A surefire way to enliven a preppy outfit in cooler months, tweed in any capacity is a welcome addition to a prep’s wardrobe.

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

1. Girly Blouses 

Look for feminine blouses that are roomy enough not to split apart at your chest but not so loose that they’re challenging to tuck into skirts and pants. Pay attention to how translucent your blouse is — a sheer blouse is great, 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 look. Accessorize with pearl earrings. 

For the most versatility, look for shirts with aligned 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 load up on inexpensive pairs of tights, I recommend getting at least one mid-priced name-brand or department-store pair. (The ones from Amazon above are high quality. I also recommend Hue tights on Amazon.) 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? Fake one with:

• Black blazer

• Pair of black pants

• Black pencil skirt 
  
  

Blazers look fantastic over sheath dresses. Complete the look with:

• Printed scarf

• Watch

• 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 the kind with cute graphics you’d find at J.Crew — are a great alternative to girly blouses during chilly fall and winter months. I prefer to hand wash and air dry mine to preserve their perfect shape and softness.  

Pro Tips  

I’ve been really into sweaters with animal graphics on them. Pair one with:

• Colored skinny jeans

• Ballet flats

• 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 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 on a headband with a ponytail to mask greasy roots. Bow headbands are bold but look adorable when styled correctly. The key is not pairing them with too many 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. (See our guide to preppy hairstyles for more ideas like these.

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. I find them much more comfortable than regular heels since they fit well around your ankle. 

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

• Pearl necklace

• Structured purse
  
  

Mary Jane’s heels look 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 outfit — even scrubby jeans and a t-shirt — look polished and intentional. A pearl brooch pinned to the lapel of a blazer or used to hold a scarf in place will look unexpected and editorial. A long string of pearls around your neck will give you that preppy style and look fantastic with any LBD or sheath dress—Holly Golightly.

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. Freshening up this piece with well-placed accessories is the key to keeping it from looking boring or stuffy. 

Pro Tips 

Sheath dresses are ideal for formal occasions because they’re thick and structured. Pair one with:

• Mary Jane heels

• Long necklace

• 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 

Those J.Crew-inspired bubble necklaces are popular preppy style picks, and for good reason! Wear one with:

• Thin sweater

• Chambray shirt

• Sheath dress

• Open blazer
  
  

The options are endless. I’ve always loved the look of wearing a long necklace with an infinity scarf or a triangle-shaped patterned scarf. Ensure they’re two distinctive lengths to see the necklace and the scarf. Nautical-inspired chain necklaces are perfectly preppy and will look great in 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

• Headband

• Mary Jane heels
  
  

11. Ballet Flats  

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

Pro Tips

I prefer inexpensive flats found at places like Target and Gap. Flats are thin-soled shoes that wear out fast, regardless of your chosen brand. Speaking of which, Tory Burch flats are a forever favorite. I loved the first pair I owned — they were black and quilted and didn’t have elastic at the heel. 

They were so comfortable that I wore them almost every day! They were disintegrating on my feet. I have a new pair of Tory Burch Revas now, but the elastic at the heel makes them hard to wear for long periods. Be sure you want a pair before making this big investment! Swap this piece out for penny loafers if you lean more towards the preppy side and less towards girly.

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 

Cape-style coats are unique, luxurious, and a conversation starter. 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 will wear:

• Dresses

• Skirts

• Pants

• Leggings

• And more 
  
  

I love patterned pea coats, tweed versions, and faux fur trimmed styles. A great winter coat is a key to looking polished on frigid, windy days. You could wear three grubby sweaters and elastic sweatpants, but a great coat 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

• Statement necklace 
  
  

Cardigans look fantastic with girly ruffled blouses peeking through. Try one with a lace cami and a pencil skirt! Forever 21 sometimes has:

• Thick cardigans

• Ribbon lining

• Jeweled buttons 
  
  

That looks almost Chanel-like. If you come across one of these, pounce 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 that they won’t take away from the other elements of your ensemble. They’ll give you shape and look 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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11 Ways to Get the Preppy Look for Kids

1. Chino: The Preppy Pants for Kids  

Chinos are a great addition to a boy's closet for those moments, particularly approaching Christmas when he needs to add a smart touch. These cotton blend pants are perfect for playtime as they’re stretchy and supremely washable.  

2. Button Up: The Preppy Shirt for Boys  

There’s something about a boy in a button-up shirt that’s just adorable. Whether you choose from:

• Check

• Gingham

• Plaid

• Plain
  
  

When worn open over a plain tee in early fall and, come winter, under a sweater, they will look brilliantly smart.  

3. Mixing in Schoolwear for Preppy Outfits  

Don’t be afraid of borrowing staples from the school uniform range. Pretty blouses, classic sweaters, and cardigans are the epitome of preppy and look great mixed with cool skirts. Because it’s schoolwear, you get all the added innovations (like non-iron shirts), so they’re super-durable and easy to wash. 

4. Tartan: The Preppy Print  

Tartan is a key addition to the preppy look, whether it's a shirt or skirt. But there are a couple of rules: don’t overdo it; one item is enough. Pair with neutrals (grey, black, white) to keep the look sleek. This skirt is a skort (a skirt panel at the front over shorts), which makes it brilliant for tree climbing and handstands.  

5. Switching in Polos for Preppy Outfits  

Polo shirts add instant prep to jeans, and they’re just as durable and comfortable as a tee. The secret to ours is the cotton mix, which gives them extra stretch, adding to the comfort factor and making them easy to wash and tumble-dry too. Top tip: if he lets you do up the top button to be extra smart.  

6. Corduroy: A Great Fabric for Fall  

Timeless, durable and preppy, cord is having a moment in kidswear. It’s a great fall material, and this green pinafore is the perfect piece to buy now as it’s easy to layer and will look just as cute in the winter as a sweater worn over a sweater with tights and ankle boots.  

7. Muted Colors for Preppy Style  

Kids look brilliant in bright colors, but if you wish to keep the look classic, go for fall shades (navy, deep red, bottle green, mustard yellow, and rust). A bonus: these colors don’t show up dirt as much.   

8. Footwear for Preppy Style  

Ballet pumps, monochrome high-top sneakers, plain ankle boots and brogues are the preppy footwear of choice. For your peace of mind, our suede shoes and boots are treated so they’re water-repellent, meaning they’ll stay smarter for longer.  

9. Adding Sparkle to Preppy Outfits  

Glitter and sequins are too fabulous to leave out of the preppy look, so add in sparkly sneakers, bags, gloves, and scarves. If the outfit is simple and classic, like this awesome spotted romper, adding some sparkle won’t stop the look from being smart.  

10. Collegiate Style for Preppy Looks  

College-style baseball jackets, cardigans, and sneakers with contrasting trim, especially for kids. It never fails to look cool and gives their outfit a smarter vibe.  

11. Layering for Preppy Style  

Preppy is a practical style trend in fall and winter as it’s all about layering, particularly for boys. Whether it’s shirts over tees, cardis over polos, or sweaters over button-ups, layering takes their look bright and adds detail. 

Generally, only have a pattern (check or stripe) on one of the layers and keep the block color neutral—blue, black, grey, or white. Layering means you can strip it off or add it on—very handy for active kids. 

The 4 Hottest Preppy Trends in 2024

1. The Preppy Evolution: From Classic to Contemporary

Preppy fashion has evolved significantly over the last century, shifting from the style of Ivy League students to a mainstream trend. 

The rise of old money and street style again influences the preppy aesthetic. It’s cooler and less polished, offering plenty of room for self-expression. 

2. The Preppy Trends Taking Over 2024

In 2024, the preppy style is about:

• Comfort

• Nostalgia

• Association 
  
  

with elite academic institutions. The comeback of logos, especially those reminiscent of school uniforms, has been a major trend in the genre. Another key preppy trend is the up-to-date take on classic pieces, which today feature modern cuts and colors that differ from what was popular in the 2000s. 

3. Must-Have Preppy Items to Add to Your Wardrobe

Nothing screams preppy fashion more than a collar from a V-neck sweater or cardigan. Polo shirts and collared tops are basic feminine garments ideal for achieving this style, especially in light, pastel shades or featuring discreet patterns, such as stripes. 

Cardigans and sweaters are also significant protagonists in the preppy aesthetic, even more so if they have a classic cut and neutral, light shades of:

• Blue

• Gray

• White
  
  

When they want a more contemporary preppy look, the youngsters go for collared crop tops, fitted shirts, and maxi or oversized sweaters, which had already become a must-have in previous seasons. 

Preppy Accessories 

When creating an up-to-date preppy outfit, young women add items and accessories that recall the world of colleges and universities, such as:

• Iconic white socks

• Stockings

• Tights 
  
  

often worn under a pleated miniskirt to give Baby one more time vibes. A preppy look, whether chic or casual, is only complete by adding the right accessories:

• laces and ribbons

• both on the hair and around the neck

• Pearls

• Scarves

• Striped scarves 
  
  

In winter and Ray-Ban Wayfarer-inspired shades in the spring and summer. 

Key Accessories for Classic Preppy Style: Bags and Shoes

For women with a classic style, a bag is a crucial accessory, and preppy lovers know how to make it the center of their outfits. Replicas of the iconic 2.55 by Chanel or the Kelly by Hermes have always been in high demand and have become a real preppy trend in 2024. 

As with bags, shoes can make or break the whole aesthetic. Mary Jane style:

• Flats

• Ballet flats

• Moccasins

• Loafers

• Golf

• Tennis 
  
  

Shoes made in canvas or leather are all the go-to for the next season. 

Overcoats for a Preppy Look 

Everything worn on top is necessary to recreate a preppy look in the cold seasons when fashionistas like to have the most fun. Preppy-style outerwear is classic, of course, but it’s about the classic pieces that only young people would wear; it’s more daring, allowing one to experiment with colors and textures while maintaining its feminine, fun, and comfortable features. 

Blazers, in all shapes and forms and, above all, in all shades, perfectly fit into a preppy outfit, especially those navy-blue showstoppers with golden buttons. Double-breasted blazers are also an evergreen piece—with perfect geometries and adaptable to different physiques, they suit everyone while also landing a posh, refined look. Classic-cut beige trench coats, university-style bomber jackets, and single-color or checked cloth coats are also chosen to elevate the look and hint at the British heritage of the style. 

4. The Return of Logo Mania

A discussion of the top preppy trends of 2024 would only be complete by mentioning the massive comeback of logos that are now sought-after, especially by younger customers, to mimic the initials of a school or fraternity typical of school uniforms in the US. In 2024, this style differs from what can be seen in the TV shows from the 2000s. 

It still brings a classic flair inherited from old-school British garments. It pushes the boundaries for a chic and transgressive result: 

• Sporty touches

• Colors

• Mix and match

• Unexpected details
  
  

Like in old fashion, logos adorn the back or front of hoodies and sweaters and the pockets of polo shirts, but they can also become a full-on pattern to create unique pieces inspired by the street style.


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7 Essentials Defining Modern Preppy Style

1. The Loafer

Loafers showcase the preppy look's evolution from stiff and proper to relaxed and cool. They've been reimagined in endless ways: 

• Chunky

• Platform

• Lug-sole versions

• Patent

• Suede

• Leather finishes

• Colorful and printed styles 
  
  

The best part? They go with everything from jeans to dresses and shorts to tailored trousers.

2. The Nylon Bag

Nylon bags are the new status bags for preppies. Forget about quilted and pearl-adorned styles. The modern prep wants a classic nylon tote, like a Longchamp Le Pliage or a Prada re-edition. These unfussy bags are practical, easy to clean, and effortlessly elevate any outfit. 

3. The Ballet Flat

Ballet flats are making a serious comeback this season. The classic style is a mainstay of the preppy aesthetic and offers an easy way to polish up any look. For fall, try pairing them with argyle or plaid socks and a pleated mini skirt for a cute collegiate vibe. 

4. The Tennis Necklace (or Bracelet)

This country club staple isn't behind wrought-iron gates and under a polo shirt. Casual, unpretentious styling is on the rise and renewing our interest in this prep classic: You're as likely to see icy tennis necklaces in a tangle of chains and pendants as you are to see them sparkling by themselves. 

5. The Pleated Skirt

Pleated skirts have long been a hallmark of private school dress code etiquette, but the newest iterations are about breaking the rules. Miu Miu makes a handful in varying hem lengths:

• Short

• Super short

• Super

• Super short
  
  

Chopova Lowena makes the alt-punk girl version with a thick leather carabiner belt and a mishmash of prints and plaids. And Thom Browne makes a gray version with his signature white stripes that would probably go over well at boarding school until you style it with a black leather lobster bag. Any of them will help you live out your rebellious teen dreams as an adult.

6. The Chino Pant 

The prep revival isn't just bringing chinos back; it's reclaiming them. Leg shapes are getting wider (like jeans), and pockets are getting more profound and more cargo-adjacent. 

Even with basic clothing like a plain white T-shirt, a directional belt, and one of the best loafers above, these casual-cool pants feel miles away from the school and pharmacy uniforms where they spent most of the 2000s—but they're still functional. 

7. The Sweater Vest

Sweater vests are the versatile little layer that every corner of modern prep seems to embrace, from dark academia with:

• Button-down

• Black watch tartan pleated skirt

• Chunky loafers
  
  

From grandpa-meets-Gen-Z-chic (with a contrasting striped shirt and chinos) to sexy yet preppy (with low-rise denim and nothing underneath). These outfits are connected to the hallowed outfits of prep's origins but are just as likely to be worn by present-day style icons like Bella Hadid and Harry Styles. 

20+ Chic and Classy Preppy Outfit Ideas for Women

1. Pleated Skirt, Sweater + Boots Outfit

A pleated mini skirt is a staple for preppy style. Its school/academic vibe makes it the perfect piece of clothing to incorporate into a preppy outfit. You can wear a pleated mini skirt with anything, but it looks especially good paired with oversized sweaters, like the oversized sweater vest in this particular outfit.

2. Oversized Blazer + Knee High Boots Outfit

Blazers are another big stable of preppy fashion. They’re super reminiscent of the old academic style. It’s super cool that more women are now embracing blazers, and it seems like each has put its own chic and modern twist on the piece. An oversized blazer cinched with a belt is just a chef’s kiss. It’s so good, especially with sheer tights and some knee-high boots.

3. Turtleneck Sweater + Pleated Plaid Skirt

Pairing a turtleneck sweater with a pleated plaid skirt gives you the preppy aesthetic outfit you can wear anywhere. It’s cute, casual and chic.

4. Oversized Sweater Over Jeans Outfit + Loafers

Loafers like the ones in this outfit give off that private school aesthetic if that even makes sense. Tied in with an oversized white collared shirt layered under an oversized sweater, they make for a pretty stylish preppy fit.

5. Sweater, Shorts + Red Boots Outfit

Cricket sweaters (is that what you call them? You know, the sweaters with the stripes around the collar and bottom?) have something about them. 

As soon as you put one on, you’re suddenly this fun, playful, sophisticated person! They’re so chic! And you can style them up like any other sweater, like in this outfit, with a pair of shorts and a lovely pair of red boots.

6. Cardigan and Plaid Pants Outfit

This outfit is like the perfect casual preppy aesthetic outfit. Plaid pants deserve more love. They’re super stylish if you give them a chance, and they look good, especially when paired with chunky boots like Doc Martens.

7. Pleated Skirt + Lettered Sweatshirt Outfit

This is like the fun and playful version of a preppy outfit. This lettered sweatshirt and pleated skirt outfit with sneakers has all the elements we’ve learned and love about the preppy aesthetic. It’s an outfit that’s not taking itself too seriously, is easy to put together, and is so cute and fun.

8. Polo Shirt and Belted Shorts Outfit

A polo shirt tucked into a pair of belted shorts and loafers is a gorgeous combination of pieces that would otherwise be so simple.

9. All Black Cropped Sweater and Pants Outfit

This is preppy but on an elevated level and with a modern twist. A cropped blazer paired with loose trousers is chic and modern, especially with shoes like the Converse sneakers.

10. Collared Shirt Under Sweater with Plaid Skirt and Red Boots Outfit

Beige goes so well with preppy or academic aesthetics. There is something about the neutral color that just blends so well with this type of aesthetic. Something is to be said about an outfit made up of a beige sweater and plaid mini skirt of the same color. All beige outfits are just so chic.

11. Oversized Shirt and Sweater with Shorts and Boots

We’ve firmly established that oversized sweaters and sheer tights are a staple for preppy style. We’ve also come to appreciate that there is something so stylish about layering an oversized shirt under a large sweater with the collar and sleeves peeking through. It’s a combo that’s chefs kiss so good.

12. Turtleneck Sweater, Mini Skirt + Boots Outfit

This outfit, the tight long-sleeved turtleneck top with the mini-skirt and the boots, is the perfect example of how you can do preppy without having to do too much.

13. Oversized Shirt Under Sweater + Boots Outfit

This is another example of the style that so many people love, with the white shirt that peeks over the sweater, but this is another way to style it, with some tight-fitting trousers and a pair of knee-high boots. It’s casual, stylish, and has preppy vibes.

14. Striped Sweater + Pleated Skirt Outfit

Pleated skirts are versatile piece of clothing that you can never seem to get tired of and can be styled a million different ways. When styled with chunky loafers and socks, it adds to the private-school girly preppy aesthetic.

15. White Shirt, Plaid Mini Skirt + Socks and Heels Outfit

Socks and heels are a combination I never thought would ever work together. But I guess it’s a combo that just needed the right moment. You just have to have fun with these trends, honestly, and this outfit is giving grown-up school girls but in the best way possible!

16. Leather Jacket, Pleated Denim Skirt + Boots Outfit

Another way to wear a pleated skirt is denim, which has a different vibe, especially when paired with a leather jacket and black knee boots.

17. Vest Top, Black Skirt and Boots Outfit

This little beige vest, black skirt, and boots are outfits that are so easy to put together but can somehow encapsulate the style well. Just proof that you can participate in a fashion trend or emulate a specific style with only a few good pieces.

18. Blazer with Bodycon Maxi Dress + Sneakers

These days, you can throw a blazer over almost anything to elevate an outfit, but it does seem to work, especially with a bodycon maxi dress and sneakers. It’s combining two things that shouldn’t work but somehow do.

19. Cap, Blazer + Pants Outfit

This outfit is probably the epitome of preppy style because it combines some of the elements we’ve come to love about the style: a blazer, and some loose pants, but it does so in a fun and not at all stuffy way.

20. Oversized Sweater Vest and Boots Outfit

A loose baggy sweater vest paired with sheer tights and some boots is honestly a match made in heaven, it an outfit that’s the right amount of preppy but free-spirited!

21. V-neck Sweater and Pleated Skirt

Classy preppy style look with the V-neck sweater vest, the oversized shirt layered under and the little pleated skirt!

4 Preppy Outfit Style Ideas for Guys

1. British Preppy Style for Men 

British preppy style for men has its roots in the casual clothing worn by students at Oxford and Cambridge universities. An effortless combination of smart, professorial pieces and sporty attire characterizes this approach to dressing. 

British prep style is both aspirational and accessible. Go-tos include:

• Barbour jackets

• Blazers

• rugby shirts

• Chinos

• Repp ties 
  
  

Worsted wool, tweeds, and plaids reign supreme. Men’s preppy style also incorporates the athletic wear of Britain’s most treasured pastimes. 

Sporting Influences in Preppy Fashion: Rowing and Horseracing Inspirations

Rowing and horseracing are two prime sports that influence this aesthetic. Bright colors, striped patterns, and single-breasted blazers are preppy staples from the Henley Royal Regatta to Royal Ascot. 

Pop on a grey flannel herringbone jacket over a color-block rugby shirt to take this style for a spin. Round out your ensemble with midnight blue slacks and boat shoes. You can roam from the spectator stands to drinks with friends in a jiff.

Expert style tip

Did you know blazers were first designed for rowers? Constructed from flannel with a loose cut, these iconic jackets also came in various colors and patterns. These distinctive coats allowed you to easily spot your team during races. Before long, the outerwear that kept rowers warm during early mornings on the water made it to dry land.

2. 80s Preppy Style for Men 

The prep movement gained a strong foothold in men’s fashion over the 20th century. American prepsters, including President John F. Kennedy and Hollywood legend Paul Newman, were popping up all around. Styles were spotted on:

• Campus

• In the office

• At the stadium

• Everywhere
  
  

Enter 80s preppy style. This era of men’s fashion, known for its bold designs, accelerated the boundaries. With sportswear designers like Ralph Lauren emerging, affordable luxury in brightly colored polos and crew neck sweaters became accessible to everyone. 

Modern Preppy Essentials for Men: Polos, Pants, and Classic Accessories

Preppy outfits for men from this decade include khaki pants or shorts paired with bright polo shirts. 

• To finish this look? A pair of topsiders and a cable-knit sweater tied around the neck. Classic color combinations comprise petal pink with kelly green and soft yellow with bright blue.

• Looking for a more contemporary take? Swap the sweater for an on-trend and slightly oversized sweater vest.

• Not ready for polos in lively and luminous hues? Opt for neutrals. 

• The preppiest of them all? Hands down, a chambray shirt. This lightweight cotton fabric goes with everything and is equally polished and relaxed. A prep must.
  
  

3. Southern Preppy Style for Men 

Let’s head south to Palm Beach. Southern preppy style starts in this well-heeled Florida city by the sea. The coastal elements found in preppy style for men are right at home here. This southern sensibility boasts pastel colors and lightweight materials. 

Madras and seersucker are key fabrications that offer tons of polish and sophistication while keeping you cool. These lightweight cotton are breathable, making them ideal for warm-weather wardrobes. 

Summer Preppy Style for Men: Madras Shorts and Suede Bucks

Traditional plaids and stripes reinvented for summer? Sign us up! For a southern preppy style outfit for men, don bright Madras shorts. Balance out the punchy plaid hues with a solid linen button-down shirt and buck. 

What are bucks, you ask? A staple in any prep’s shoe collection, summery suede bucks or Oxfords are lace-up shoes with a rubberized sole. We recommend a no-show sock to pull off the sockless look that prepsters rock all summer. That’s a way to put a little prep in your step.

4. Preppy Style for Winter 

There is no shortage of activities to keep a prep entertained during winter. While the hours of sunlight may be minimal as the mercury dips, the season is filled with merriment. From fireside holiday gatherings to braving the chill when hitting the slopes, a preppy style for men in winter is something to dress up for. 

This time of year lets you showcase the best of your wardrobe. From longline camel hair coats to waist-skimming peacoats, there is a layer for every occasion. Don’t forget about your accessories. Remember to wrap a plaid scarf around your neck and tuck a pair of vegan leather gloves in your pocket. 

Holiday and Winter Prep: Classic Looks with Seasonal Flair

The winter holiday season offers an opportunity to have fun with color, pattern, and textures. When thinking about how to dress for a holiday party, stick with the classics. Just add a little flair. Give your khakis a break and start your look with a pair of dark green corduroys add:

• Striped button-down shirt

• Cozy shawl cardigan

• Chukka boots for any seasonal shindig. 
  
  

Heading to the mountains to celebrate the New Year? Meet friends at the base of the mountain for an après-ski drink. Wear a black toasty turtleneck sweater with performance pants in a pop of color. We love a burnt orange or bold burgundy. Simply add a puffer jacket and boots. See? Your preppy-style men’s wardrobe can traverse winter outings with ease.

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• Preppy Hair Colors
• What Colors Are Preppy
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33+ Timeless Preppy Fashion Brands For Every Budget

Selecting the right brands is key to achieving a preppy look. Preppy clothes are often associated with specific brands that have a classic and collegiate style. You can find items at other stores, but choosing the right brands will help you nail the preppy look. 

1. Brooks Brothers

If you’re looking for ultra-preppy style and classic outfit pieces, Brooks Brothers is your place. I don’t shop here often because it’s super expensive, but this is the OG preppy store if you want to dive into true old-prep. Pricing: Expect to spend $200+ per item. 

2. Ralph Lauren

One of the most classic preppy-style stores on this list is Ralph Lauren. It’s known as one of the basic preppy fashion stores for a reason! 

The best part about Ralph Lauren? It offers really beautiful items with a vintage vibe. These preppy items aren’t trendy prep or fads, they’re the real deal. Pricing: Most items are well over $200; expect to spend $300-$600 per piece on average. 

3. Tory Burch

Although Tory Burch is known for the classic flip-flop sandals, this preppy style brand offers many other popular pieces, too. You can shop for super cute preppy bags at Tory as well as a variety of shoes and clothing.

I especially love the classic and preppy clothing for all four seasons. Pricing: Expect to spend $150-$500 per item. 

4. Alice + Olivia

If you like trendier preppy outfits then you’ll love Alice + Olivia. This preppy fashion brand has super cute sweaters, interesting tops, and pant sets. 

I purchase a few pieces a season to add a bit of spice to my preppy wardrobe items. Pricing: Most pieces sell for $100-$300. 

5. Eastland Shoes

I love Eastland Shoes for preppy, durable, affordable shoes. I especially enjoy the:

• Loafers

• Oxford shoes

• Slip-on 

• Boat shoes for women
  
  

Pricing: Most pairs of shoes are well under $100. They last for a long time and are comfy! 

6. Patagonia

Patagonia is a great winter brand if you want the woodsy/preppy style vibe. Everyone should own a Patagonia pullover. 

They’re truly amazing! This preppy-style brand sells all sorts of fleeces and jackets. Pricing: Expect to spend at least $200 per item. These pieces are incredibly warm and made for the outdoors, not just for the look. 

7. Theory

Theory is a great mid-range designer fashion brand for classic preppy outfits. I typically shop in the best-sellers section. I like the:

• Cardigans

• Blazers

• Tailored pants

• Classic blouses 
  
  

The theory has a business/preppy style vibe, so it’s a great place for professional preppy outfits. Pricing: Expect to spend $300-$700 per item. 

8. Target

Surprisingly, Target sometimes has great preppy-style items, but you definitely have to sort through them. Target started its preppy vibes with the Lilly Pulitzer at Target collection. It sold out quickly, but they still have some great budget pieces. 

I shop for preppy:

• Dresses

• Shirts

• Blouses

• Fabric shorts 
  
  

Target occasionally has super cute lookalike preppy shoes, too. Pricing: I usually spend around $20 per item at Target. 

9. Barbour

This classic England-based brand is woodsy-preppy style, so it’s perfect for every season. You can find entire preppy outfits at Barbour; all you need is a hunting dog to complete the look. 

This preppy brand has so many great items for women. I love the quilted coats, vests, and boots. Pricing: Most Barbour items are over $100, but the quality is impeccable. These are all long-term items. 

10. Abercrombie

I have always loved Abercrombie since it was super trendy when I was young, but now I love this brand specifically for preppy outfits. If you’re looking for preppy-style pieces at Abercrombie, check out the:

• Shirts and blouses

• Sweaters and vests

• Dresses 
  
  

Especially during the spring and summer. Pricing: I try to shop the sales at Abercrombie and spend no more than $30 per item. For something I love, I will spend up for $50 or $60. I can typically find full preppy outfits at Abercrombie for a reasonable price.

 

11. Everlane

If you like simple preppy style then you’ll love Everlane. It’s a brand that’s all about clean lines and high-quality items. Everlane is a great preppy fashion brand for the basics. I typically check out the best sellers and shop for:

• Cotton t-shirts

• Sweaters

• Jeans

• Sneakers
  
  

Pricing: Most items are well under $100. Sometimes, you can get basics (like shirts and sweaters) for $20 per item. Keep in mind that these are super high-quality cotton pieces! They will last for a while. 

12. Kate Spade

If you want a girly yet classic preppy fashion brand, you’ll love Kate Spade. I (of course) love every Kate Spade handbag out there, but I also love this brand’s shoes (especially the darling flats) and the super sweet, girly accessories. 

13. L.L. Bean

Most preppy people have at least a few items from L.L. Bean. It’s a solid, mid-range store that sells quality pieces. L.L. Bean is great for all your basics, from preppy pullovers to sweaters and jackets. I especially love the bean boots. Every preppy-style aficionado needs a pair! 

14. Longchamp

Longchamp is technically a French fashion brand but is also very classic and preppy. Every truly preppy woman should own a Longchamp bag. I have the classic bag in both blue and black, size large. 

It’s such a fantastic bag because you can just throw it in the wash if it gets dirty. This is a great bag for all seasons and doubles perfectly as a beach bag! 

15. Jack Rogers

This is another super classic preppy brand. I rarely wear a Lilly Pulitzer dress or top without my Jack Roger sandals. 

Even though the classic sandals are super popular and gorgeous (I have them in white, gold, and navy), Jack Rogers has many super cute sandal styles. 

16. Hunter

Hunter rain boots are classic, preppy-style shoes that are essential for any season! I have the classic rain boots and the short ones in navy, green, and red. 

There are many different options depending on your style and height! Remember that the classic high boots might be too tall if you're on the shorter side. My sister is 5’4″ and likes the medium size.
 

17. Southern Tide

If you’re looking for a classic country club style, Southern Tide is your preppy style brand of choice. I love all of the best sellers!

 This is a good place to start. The dresses are gorgeous and can be worn in many ways, but Southern Tide also has cute pullovers, sweaters, and more. 

18. Love Shack Fancy

Although Love Shack Fancy has some frilly, girly dresses, they also have some preppy pieces that are perfect for summer. I typically shop at Love Shack Fancy for bright summer dresses in:

• Yellow

• Blue

• Pink

• Green tones
  
  

These dresses pair with Jack Roger sandals and some preppy jewelry. 

19. Talbots

Talbots is a great mid-range preppy style brand for all ages. I love shopping for my basics at Talbots, including sweaters and blouses. I also love the tailored pants and sneakers. The whole outfit I’m wearing in the photo is from Talbots, including the shoes and the bag! 

20. Lacoste

Lacoste is a cool, casual, preppy fashion brand with vintage vibes. There are so many great pieces at Lacoste! 

The logo itself is enough of a reason to buy these pieces, but I especially enjoy shopping the best sellers, including the polos, polo dresses, and pullovers. 

21. J. Crew

J. Crew is another classic store for basic, high-quality, preppy outfits. I recommend starting with the best sellers. You can find:

• Gorgeous blazers

• Tailored pants

• Preppy style dresses

• Button-up shirts

• Flats 
  
  

22. Marley Lilly

I love Marley Lilly when I’m shopping for monogrammed items. Literally everything on the site is adorable, but I typically either check out the best sellers or shop for monogrammed bags, shoes and socks, and clothing (including pullovers, long-sleeve t-shirts, and comfy shorts). 

23. Gap

Gap is a great mid-level brand for affordable but quality items. I typically shop for my blazers, jackets, and coats at Gap. I just got a super cute trench coat that’s very fashionable and preppy. The dresses and sweaters are also quite darling and preppy. 

24. Old Navy

Old Navy is a super budget-friendly preppy style brand for seasonal basics. I shop at Old Navy for:

• Feminine preppy blouses

• Simple sweaters

• Basic jeans (especially white ones)

• Linen/fabric shorts 
  
  

25. Lilly Pulitzer

Ah, Lilly P. There is nothing like the bright, happy patterns of Lilly Pulitzer! I make it a point to add at least one Lilly item to my wardrobe every summer. I love wearing Lilly dresses to weddings, out to dinner, or even to a summer brunch by the water. I love literally everything at Lilly Pulitzer, I tend to shop for both formal and casual dresses, floral blouses (they pair wonderfully with white jeans), patterned swimsuits, and rompers. 

26. K.J.P.

I’m obsessed with K.J.P. pieces! They’re very seasonal, classic, and high-quality. The best preppy fashion brands for preppy style | Preppy brands for a preppy clothing wardrobe I especially love women’s dresses, thick knit sweaters, and delicate gold and pearl jewelry. 

27. Sperry

Virtually everyone has heard of Sperry. However, this preppy fashion brand sells more than classic boat shoes. 

28. Tommy Hilfiger

Tommy Hilfiger is another classic brand that’s a bit more affordable. You can certainly shop for the most classic Tommy pieces, such as:

• Sweaters

• Jackets

• Button-up shirts
  
  

But you can also find some cute seasonal items at this preppy fashion brand. 

29. Mark and Graham

Mark and Graham is the preppy fashion brand for you if you want preppy luggage and/or bags. These are the most classic preppy luggage pieces that can be used repeatedly! 

I shop at Mark and Graham for luggage as well as totes and bags. Their products can be monogrammed or used plain. 

30. Tuckernut

I love shopping for spring and summer preppy-style pieces at Tuckernut. They have the most darling items! 

If you’re looking for the Lilly Pulitzer look, only toned down and a bit more classic, Tuckernut is your preppy fashion brand. 

31. Vineyard Vines

If you love preppy fashion, you know Vineyard Vines is one of the OGs. This is where to start when assembling preppy outfits. 

Whether you want to shop for:

• Preppy-style dresses

• Button-up shirts

• Cozy pullovers

• Swimsuits

• Fabric shorts

• White pants

• Bags

• And more 
  
  

Vineyard Vines has it all. Owning a few pieces you’ll wear often is worth the investment! 

32. Cartolina Nantucket

When it comes to curating my preppy wardrobe, Cartolina Nantucket is my top pick. With a penchant for classic New England flair, this brand effortlessly captures the essence of timeless style while keeping my budget intact. 

33. J. Crew Factory

J. Crew Factory is the best preppy fashion brand for high-quality items if you're on a budget.

Try AI Personal Color Analysis For Free Today

The preppy aesthetic is all about classic colors and patterns. Think navy, burgundy, hunter green, and other earthy tones. When the leaves start to change, it’s time to swap out those bright summer colors for a more muted, autumnal palette. If you want to know exactly what colors will look best on you this fall, check out WhatColors. 

This app analyzes your unique coloring to find your ideal seasonal palette and nail colors. With WhatColors' AI personal color analysis app, you can get your color analysis done within 60 seconds. 

Download our app for free today on the App Store or Google Play store.