The preppy aesthetic is all about style, class, and sophistication. And curating a wardrobe that embodies these qualities takes time, effort, and money. First, you need to research the best preppy brands. Next, you must focus on timeless styles and classic pieces that reflect your taste. If you want to start your journey toward a more preppy wardrobe, you're in the right place. This article will help you discover and integrate the best preppy brands into your style to achieve your goals effortlessly.

One way to make this process easier is to use WhatColors' AI personal color analysis app to identify your true colors. This tool helps you uncover which shades suit you best and find the preppy brands that align with your aesthetic and elevate your style. 

Table of Contents

• What Is Preppy Style?

• Who Is the Preppy Style Most Suitable For?

• 15 Key Wardrobe Essentials for a Preppy Style

• How to Create a Preppy Style

• 24 Best Preppy Brands For Men (And Why You Should Wear Them)

• 34 Preppy Clothing Brands To Elevate The Preppy Woman's Wardrobe

• 7 Great Preppy Shoe Brands to Wear with Your Preppy Clothing

• Try AI Personal Color Analysis For Free Today

What Is Preppy Style?

The preppy style is timeless. Cardigans, polo shirts, and Mary Jane shoes, all staples of the fashion, will never truly go out of style. American prep style has survived brand bankruptcies (J. Crew emerged from bankruptcy in 2020), store closures, the rise of athleisure, and hype beast trends. Is it secret to remaining relevant? Preppy style has learned to adapt and evolve with the times.

From its not-so-humble beginnings in the 1890s and early 1900s to a revival in the 1980s and 1990s, it’s evident that the preppy lifestyle isn’t going anywhere. Even today, we still love preppy style, as evidenced by the following:

• Celebrities such as Victoria Beckham and Yara Shahidi

• Designers like Chanel and Ralph Lauren.
  
  

The Origins of Preppy Style

Back in the late 1890s and early 1900s, the preppy style was a status symbol worn by wealthy guys who went to preparatory and Ivy League schools, hence the name. Brooks Brothers button-downs, 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 the preppy style, and we really never looked back.

The '50s: The Rise of Preppy Style

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

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: Preppy Style Hits Mainstream Culture

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

• Khakis

• Plaid blazers

• Knotting sweaters
  
  

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 Shrunken Twist on Preppy Style

The late '90s brought a new, skinny twist to preppy style. Pants were lower, boot cuts were in, and Britney Spears turned looking like a sexy schoolgirl, complete with a white button-down and pleated skirt, into a significant thing. 

While oversized grunge had a moment during this decade, some preppy elements, like all the plaid and knotting shirts, 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 cast members of Dawson's Creek.

The 2000s: The Preppy Style Gets a Makeover  

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 made it clear that the preppy style has gone through yet another metamorphosis. Shows like:

• 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.

Who Is the Preppy Style Most Suitable For?

The preppy aesthetic has a distinct target audience. This niche style is popular among the upper-middle to upper class, especially those who are part of the elite or aspire to be. The look is associated with the American rich, particularly those with old money. Preppy people love classic styles, especially those that evoke Ivy League colleges and the students' lifestyles. Preppy clothing brands sell timeless pieces that can be worn for years or even decades without looking dated. 

4 Signs You’re A Prep 

If you want to determine whether or not you are an actual prep, check out these points and see if they apply to you.

1. You Love The Classic Look 

Do you prefer styles that stand the test of time over fashion trends? Indeed, the preppy style is the perfect match for you because timeless pieces characterize preppy outfits. 

2. You Have An Old-Money Lifestyle 

If you love furnishing your home with elegant home decor and spending your Sundays talking about my favorite tennis players, the preppy style will fit your old-money lifestyle! 

3. You Love Neutral Colors 

The preppy style is excellent if your primary color palette is black, white, navy blue, grey, and other light colors. These are the colors associated with American collegiate charm. 

4. You Are Not Into Fast Fashion 

Do you avoid buying from fast fashion brands that follow fleeting trends? If so, the preppy style is definitely for you. Preppy fashion is all about quality and timeless style. True preps only buy clothes that are made to last, not only in quality but in style.

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15 Key Wardrobe Essentials for a Preppy Style

1. Oxford Shirts: The Preppy Essential

An Oxford shirt is the most dependable piece in your closet. These classic cotton shirts come in various colors, and they instantly elevate your look with a preppy vibe. Style an Oxford shirt with khaki pants or a pleated skater skirt and a belt for an outfit that is equal parts smart and stylish. 

2. Blazers and Rowing Blazers: The Preppy Go-To

Blazers are tried-and-true pieces that are an integral part of the preppy style. They’re versatile but look remarkably polished when worn with a collared shirt. For extra preppy points, go for a rowing blazer with a patch. 

3. Khaki Pants: The Ultimate Classic

Khaki pants are one of the best purchases you will make for your preppy wardrobe. They will see you through so many seasons. Khaki pants are often worn with white button-down shirts and loafers for a classy style. 

4. Loafers: The Preppy Shoes

If there is a pair of shoes that screams preppy style, it’s loafers. You honestly can't go wrong with loafers. They work with any preppy outfit, from straight-leg jeans and an Oxford shirt to elegant skater skirts and tights. The style possibilities are endless. From Margot Tennenbaum in her GH Bass Wejuns to a cadre of editors, stylists, and Upper East Siders in Gucci Jordaans, loafers are one of the prep's universal accessories. 

These intelligent shoes have been remixed and re-remixed in infinite ways (lately, with lug sole and platform soles). Their silky-smooth leather and shiny hardware accents will forever stand the test of time, preferably with a little crew sock layered underneath.

5. White Tennis Shoes: The Classy Sneaker

Tennis shoes are another pair you need to achieve the preppy style. They effortlessly infuse an outfit with collegiate charm and casual elegance. 

6. Chinos: The Preppy Trouser

The prep revival isn't just bringing chinos back; it's reclaiming them. Leg shapes are getting wider, and pockets are getting deeper and more cargo-adjacent. Even throwing them together 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. Polo Shirts: The Preppy Staple

Polo shirts complete any preppy wardrobe. They're great for creating iconic preppy outfits because they offer versatility and class.

8. Trench Coats: The Preppy Outer Layer

Trench coats are an essential addition to a preppy wardrobe. They will complete any outfit with a dress or a shirt and pants combo. 

9. Classic Belts: The Preppy Accessory

Timeless belts help to tie a look together. What's more to love about classic belts is that they work for any preppy look. 

10. Sweater Vests: The Preppy Layer

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

• A button-down

• Blackwatch tartan pleated skirt

• Chunky loafers) 
  
  

They're 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. 

11. Rugby Shirts: The Preppy Classic

Rugby shirts are tops that all the preppy style icons always have in their closet. They inject the perfect dose of class and college charm into an outfit. What's more to love about rugby shirts is that they can be styled in many ways. Wear it with your go-to pair of jeans or a skirt. 

12. Wellingtons or Rain Boots: The Preppy Boot

Preppy outfits are consistently elevated with a pair of wellingtons. They work with any preppy outfit and can be worn again, again, and again.

13. Pleated Skirts: The Preppy Icon

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. Either way, any of them will help you live out your rebellious teen dreams as an adult. 

14. 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.

15. The Ballet Flat

Prep ran (in ballet flats) so ballet-core could soar (on TikTok). The uncomplicated shoe helps you float through the day with the poise of a ballerina and the unaffected air of an Ivy League trust-fund baby. But here are some ways of styling from the recent runways that's likely never occurred to them: with chunky socks and leather hot pants or with a tiny skort and a gingham puff-sleeve blouse.

How to Create a Preppy Style

Start With the Basics

To build a solid foundation for your preppy wardrobe, you need to start with the basics. 

• A crisp, button-down shirt, a sleek black blazer, and a timeless trench coat are must-haves. 

• Loafers, boat shoes, and Oxford flats are all fantastic shoe choices for this style. 

• A-line or pleated skirts and knee-length shorts are perfect for this look.

• Pair it with some loafers or oxfords, and you’re good to go. 
  
  

Add Some Jewelry and a Classic Handbag

To complete the ensemble, add a touch of jewelry and a classic handbag. 

• Opt for simple, elegant accessories like pearl earrings or a delicate gold necklace. 

• A structured leather handbag in a neutral tone will add a nice finishing touch to your preppy look. 
  
  

Keep it simple

Remember to keep your accessories minimal and refined; this style is all about timeless elegance and understated glamor.

Choosing Fabrics Like a Pro

How preppy one should dress is a matter of style and fabric. The preppy style is all about choosing the right fabrics. 

• Fine cotton, tweed, and wool are staples in any preppy wardrobe. Choose cotton shirts, skirts, and dresses, and combine them with well-cut blazers or jackets. 

• You can also opt for a tweed jacket or skirt, perfect for chilly autumn mornings. 

• Wool is another great fabric to choose from, as it adds a touch of sophistication and warmth to any preppy outfit. 
  
  

Investing in high-quality fabrics will ensure that your preppy wardrobe will withstand the test of time and maintain its classic appeal.

Master the Art of Mixing and Matching

The goal of a preppy aesthetic is to achieve a polished, effortless look. This can be achieved 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. 
  
  

For example, 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.

Keep It Simple and Understated

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

• 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. Also, remember to keep your hair and makeup natural and minimal to maintain the effortless preppy vibe.

Embrace the Classics

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. 

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24 Best Preppy Brands For Men (And Why You Should Wear Them)

1. Brooks Brothers: The Gold Standard of Preppy Fashion

Brooks Brothers is a true American institution in the world of classic menswear. Founded in 1818, it has been making the same styles for decades, if not centuries. The label has dressed everyone from U.S. presidents to countless fictional Ivy League alumni. 

If you want to look like you just stepped out of a John Hughes film, Brooks Brothers is the brand to turn to.  You can expect exceptional quality and durability from their garments, which means they’ll last for years and never go out of style. 

2. J.Crew: Stylish Yet Affordable

American brand J.Crew was founded in 1947 by Mitchell Cinader and Saul Charles and today operates around 450 stores in the US. Its focus is style over fashion but with a distinctive preppy edge. 

In its campaign and lookbook shots, you’ll find modern pairings of sneakers with suits and brogues with jeans, alongside traditional color-blocking and pattern mixing. The quality is good, and the price point is reasonable.

3. Ralph Lauren: The Preppy King

American designer Ralph Lauren (born Ralph Lifshitz) founded the Polo Ralph Lauren Corporation in 1967. Ten years later, in 1977, the company introduced the signature cotton mesh Polo shirt in various colors. 

Featuring the now-iconic polo player logo on the chest, the shirt became emblematic of the preppy look and put Ralph Lauren on the map. Lauren himself breathed the American Dream into a clothing (and more) brand, creating the embodiment of a particular lifestyle or way of life.

4. Billy Reid: Southern Style Done Right

Southern preppy is a niche style tribe that sits in the broader Americana family, it takes classic preppy fashion but gives it a slightly looser, more casual, ranch-ready flavor. Billy Reid is its patriarch, a designer highly revered in fashion circles even if he doesn’t have the mainstream clout of a Lauren or Hilfiger. Everything you expect from the best preppy brands, especially polo shirts, button-downs, and easy-wearing shorts and trousers.

5. Aurelien: Italian Luxury at a Fair Price

The quiet luxury movement borrows heavily from some of the understated but always sophisticated preppy fashion styles. Aurelien puts an Italian spin on it with timeless garments like knitted polos, loafers, and unstructured tailoring. It’s a direct-to-consumer label, offering lower prices than some designer labels it shares factories and mills with.

6. Luca Faloni: La Dolce Vita Meets Preppy Style

Italian menswear has long remixed the staples of preppy fashion with a touch of La dolce vita. Think knitted polo shirts, unstructured blazers, and tailored chinos. Luca Faloni does all of these and more at prices lower than you’d expect for a label 100% made in Italy. 

The vibe is more tailored and summery than the classic collegiate style, but the brand also offers hoodies and sweatshirts, again given a luxe touch in beautiful knitted fabrics.

7. Pelota Sporting Clothiers: For the Athlete in All of Us

British brand Pelota designs clothes for ‘Aprés Sport’: that period where a sportsman’s endeavors end and social life begins. Inspired by some of the world’s finest ball sports – the type of games prevalent on Ivy League campuses in the 50s – expect high-quality hoodies, sweats, and tees in an athletic yet forgiving fit. The definition of athleisure.

8. Jack Wills: Heritage Meets Youthful Spirit

Jack Wills was founded by Peter Williams and Robert Shaw in 1999. The brand’s original store opened at 22 Fore Street, Salcombe, and was created to, “bottle what being at a British university was all about”. Today, Jack Wills combines heritage style with a youthful, irreverent and carefree edge. The label quickly went mainstream in the 2000s and was viewed as UK’s answer to Abercrombie & Fitch.

9. Abercrombie & Fitch: A Classic Reborn

With a long and rich heritage, Abercrombie & Fitch was founded in 1892 in New York by its namesakes, David T. Abercrombie and Ezra Fitch, developing a reputation as an elite outfitter of sporting and outdoor goods. Now, it’s more known for its racy marketing photography featuring semi-nude males and females, often employees of its stores. 

A&F’s signature moose logo was once the badge to be seen in, but its pull has since waned. However, with a change in tack in recent years, the brand has refocused on what helped made its name in the first place: high-quality preppy basics that epitomize that laid-back California lifestyle.

10. Tommy Hilfiger: A Preppy Icon

Founded by Thomas Jacob “Tommy” Hilfiger in 1985, the brand is known for its classic Americana style with a preppy twist. Hilfiger is still the brand’s principal designer despite selling the company in 2006 for $1.6bn. While the label has suffered in recent years, it has experienced a renaissance since 2017 thanks to the revival of 1990s menswear.

11. GANT: The Ivy League Look

GANT was founded in 1949 by Bernard Gantmacher as a shirtmaking company in the college town of New Haven, Connecticut. It quickly became known for its Oxford shirts, which featured:

• The perfect collar roll

• A locker loop

• Box pleat

• Back collar button

• Button tab
  
  

Located near Yale University, the US label played a significant role in shaping the Ivy League Look as we know it today.

12. Hackett: British Heritage Meets Preppy Style

Hackett was founded in 1979 by Jeremy Hackett and Ashley Lloyd-Jennings from a stall on London’s Portobello Road selling used clothes. Despite its humble beginnings, Hackett has gone on to become a stalwart of the new breed of fine British brands. 

Today, you’ll find a wide range that runs the gamut from high-quality basics to bespoke tailoring.

13. Drake’s: Timeless Preppy Accessories

Founded by Michael Drake in 1977 in London’s East End, Drake’s quickly earned a reputation for producing quality scarves and shawls for high-end fashion boutiques and traditional tailoring houses. This initial success saw the company branch out into ties and pocket squares, for which the brand is recognised. 

A philosophy of producing timeless pieces that have a relaxed elegance to exacting standards ran through Michael’s and the brand’s veins. A recipe for success in itself, Drake’s soon became a firm favorite of style tastemakers here in the UK, but never by the mainstream – intentionally, no doubt.

14. G.H.Bass: The Penny Loafer People

G.H. Bass & Co. dates back to Maine in 1876 when George Henry Bass founded the footwear company. But it wasn’t until 1936 – when G.H. Bass put a stylish spin on a Norwegian farm shoe designed for loafing in the field, dubbing them “Weejuns” that the brand went mainstream and history was made. 

Known for creating the world’s first penny loafer, the company has never looked back. Arguably the defining preppy shoe, the iconic Weejun has been a firm favorite of everyone from Ivy League graduates to the late Michael Jackson ever since.

15. Sperry: The Original Boat Shoe

Sperry is the original American brand of boat shoe, first designed in 1935 by Paul A. Sperry. Rumour has it that while sailing on the Long Island Sound, Sperry slipped on the deck of his boat and fell overboard, an experience that drove him to develop a safer, non-slip shoe. Multipurpose, the Sperry Top-Sider Deck (or boat) shoe has been seen on a variety of celebrities and presidents, including, again, JFK.

16. Beams Plus: The Japanese Ivy League

It’s an oft-repeated opinion in menswear circles that Japanese fashion didn’t just adopt preppy Americana. The classic Ivy League look of the 1960s was lifted wholesale by Japanese prepsters and brands alike, who then began crafting their versions of preppy fashion. 

Beams Plus is one of the most beloved and enduring labels for doing it. Part of a vast retail empire that stretches back to the 70s, it combines heritage menswear and rugged workwear to create its take on so-called Ametora or Japanese Ivy. Think of well-made garments with generous cuts and nerdy details.

17. LL Bean: The Great American Outdoor Brand

Founded in New England, the spiritual home of preppy fashion, LL Bean is one of the most historic and influential Americana brands, renowned for its hardy, well-made outdoor gear. It’s more rugged than some preppy labels, but the collection is also vast. You’ll find smarter chinos and Oxford shirts among the camping gear and workwear. The label does a lot of classics, but start with its chamois shirts, logo tees and quarter-zip tops.

18. Lacoste: The Sporty Preppy Brand

Preppy fashion has always been a combination of dapper menswear and classic sportswear. In that sense, Lacoste is one of the quintessential preppy brands; its famous crocodile-emblazoned polo shirt the creation of French tennis maestro Rene Lacoste. 

He wore the shirt on the court and quickly realised it looked great off-court, too. The rest is history. The brand isn’t all about the polo. You’ll also find other preppy classics in its collections, from knitted V-necks and sweatshirts to zip-up track tops.

19. Crew Clothing: Nautical Inspired Preppy Wear

Many of the best preppy labels have their roots in sport and recreation, and Crew Clothing is no different. Inspired by the British coast, it started life behind a windsurfing shop, and much of its collection is built for life on or near the water. 

Deck shoes, raincoats and beachwear are all present and correct, but it also does a good line in heritage British menswear, from stout rugby jerseys to rowing blazers. It’s also one of the most affordable preppy brands you’ll find.

20. Noah: A Skate-Inspired Take on Preppy Style

Preppy fashion is so influential that it has gone from 60s college students to 80s finance bros to 90s skate kids. The latter inspired ex-Supreme creative director Brendon Babenzien to found Noah, a New York label that lovingly recaptures the fusion between skatewear and preppy fashion. 

There’s a heavy dose of JFK-lite nautical style, plus slacks and loafers, but it’s mixed with big graphic tees and eye-popping prints. Somehow, it just works, and it’s all very, very easy to wear.

21. Ivy Ellis: Accessories for Preppy Outfits

Good preppy style is all about the little details, a fact not lost on Scottish brand Ivy Ellis. It does socks, mainly. Think throwback athletic styles from the 70s or 80s and woolen slub styles, both of which borrow from varsity colors and look great with shorts and slacks alike. Everything is made in Scotland, and you’ll feel the quality as soon as you pull them on.

22. Vineyard Vines: A Classic New England Brand

Born in Martha’s Vineyard, one of those New England enclaves where America’s well-to-do spend their summers, Vineyard Vines was born in the 90s but it’s a faithful and loving take on classic preppy style. 

It does all the essentials and does them well: 

• Polos

• Ribbed sweaters

• Button-down shirts

• Slacks

• Shorts

• Casual tailoring
  
  

You won’t find many preppy brands more authentic than this one.

23. Armor-Lux: French Nautical Style

Classic French outfitter Armor-Lux has been making distinguished, nautical-themed fashion since the 1930s. It’s best known for its near-peerless Breton tops, but other preppy must-haves include:

• Sailing-style raincoats

• Polo shirts

• Blazers

• Fisherman jumpers
  
  

With its collections still designed and made in Brittany, Armor-Lux brings a sophisticated, Gallic interpretation of preppy style.

24. Aime Leon Dore: The Modern Preppy Brand

With its lookbooks set in wood-panelled dorm rooms, cult New York label Aime Leon Dore proudly wears its preppy influences. The brand is one of a handful to have taken Ivy League style somewhere new in recent years. 

You’ll find classic sportswear and more tailored preppy pieces like tweed jackets in the collection, but it’s all mixed up with hip-hop references and streetwear. If it sounds eclectic, that’s the aim, but the overall effect is modern, urban, and classic all at once.

34 Preppy Clothing Brands To Elevate The Preppy Woman's Wardrobe

1. Tory Burch

Tory Burch supplies a delightful mix of preppy sophistication and bohemian charm. 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

• Tailored pants
  
  

2. 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

• 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.

3. 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
  
  

4. Talbots

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

Talbots is brimming with the best preppy clothes, from polished casual pieces like linen blazers, tweed collarless jackets, v-neck sweaters, and great fancy dresses.

5. Southern Tide

Southern Tide is for the fashion-forward woman who loves a preppy, 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, which became a hit in the fashion world 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 different 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

• Will shorts

• Crewneck t-shirts
  
  

6. Rowing Blazers

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

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

7. Alice + Olivia

Alice + Olivia was born out of 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
  
  

8. 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 understated 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 they are experiencing daily Sunday comfort. With the endless selection of blazers, coats, fleece tops, chino pants, and more, you can easily put together the best preppy looks!

9. 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.

10. 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.

11. 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!

12. Hunter Boots

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

13. 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. 

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
  
  

14. 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.

15. Ted Baker

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

• Tote bags

• Romantic floral dresses

• Drape-neck tops

• Slingback pumps and more
  
  

16. 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 to trench coats to sweaters and many more wardrobe classics.

17. Michael Kors

Michael Kors is 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.

18. 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 not only shaped fashion but also 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.

19. Coach

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

20. 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.

21. Nautica

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

22. 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 be satisfied with the wide selection of modern and classy pieces!

23. Cole Haan

You might not have heard of Cole Haan, but when you go through the timeless footwear the brand has, you will want to shop there. Cole Haan was established in 1928 to offer excellent craftsmanship, comfort, and design. 

Cole Haan has created shoes with a traditional American style and bold innovations for nearly a century. From loafers, ballet flats, espadrille sandals, and Oxfords, the brand has preppy footwear for formal occasions, casual outings, and more. You’re guaranteed to find polished shoes for your preppy wardrobe.

24. 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. From its signature raffia tote bags to its iconic leather footwear, Loewe is a great place to discover the best styles.

25. Mango

If Loewe is out of your budget, consider shopping at Mango. This Spanish brand has unique classic pieces without the steep price tag of some designer brands. You will find everything from:

• Trench coats

• Sweaters

• Loafers

• Classic sunglasses and more
  
  

26. River Island

Another brand to have on your fashion radar is River Island. This iconic British high-street brand was founded in 1959. Heritage styles and modern influences inspire the brand. It offers classic silhouettes that will perfectly align with your preppy style. This includes:

• Intelligent blazers

• Tailored pants

• Button-down shirts
  
  

27. 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.

28. Frank and Oak

Under-the-radar brand Frank and Oak was founded in 2012 with the idea of inspiring 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

• Straight-leg jeans
  
  

29. 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 to find 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
  
  

30. 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
  
  

31.  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 has some lovely 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.

32.  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. What sets Dudley Stephens apart is its commitment to sustainability, crafting pieces that stand the test of time in recycled performance fabrics. From turtlenecks to pullovers, shorts, and more, you’re sure to find a piece that speaks to your classic style.

33. 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.

34. 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
  
  

7 Great Preppy Shoe Brands to Wear with Your Preppy Clothing

1. New Balance Made in the UK 991: The Ultimate Preppy Shoe

New Balance has long been a classic preppy staple that can easily crossover to all walks of life, from its New England roots down to the Steve Jobs thing. In some ways, this is the ultimate preppy shoe brand. The Made in the UK 991 model is constructed in the UK, adding a layer of awesomeness. 

2. Veja RECIFE Chrome Free Leather White Black: The Sustainable Sneaker

Veja has become a favorite for the guy who wants to put a new spin on the preppy look by wearing a progressive, sustainable brand. The RECIFE model will give you that sleek, not-trying-too-hard look. 

3. NikeCraft Tom Sachs General Purpose Shoe: The Coolest Sneaker

Nike Tom Sach's General Purpose is the most preppy shoe you can buy, period. And it works great with your preppy outfit, as well. You will see me wearing this shoe at some point, I promise. Lucky for you, while the Mars Yard was borderline unobtainable, this will be restocked regularly, according to Sachs and Nike.

4. OFFICINE GÉNÉRALE -Brown Suede Mika Penny Loafers: A Preppy Classic 

The penny loafer is a preppy shoe staple for men, and it is having another big moment. Pair it with crisp selvedge denim to get an elevated preppy look. Officine GÉNÉRALE makes fantastic shoes, including these.

5. Yuketen Full-Grain Leather Boat Shoes: A Preppy Essential 

Yuketen is hand-making many of their shoes in Maine, harkening back to the glory days of the craft in places like Skowhegen and Dexter. These full-grain leather boat shoes can be your absolute go-to kicks for preppy situations.

6. Saye Modelo '89 Vegan: Stylish and Eco-Friendly 

Beautiful sustainable shoes here from Saye, pull these out to get the maximum laid-back preppy style.

7. Birkenstock Clogs: Versatile Preppy Footwear 

Birkenstock clogs, are some of the most versatile shoes going, as they go with any style of dress. Preppy is no different; these will elevate any preppy look. These green ones will certainly help you own the day with an extra splash of color, in suede.

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