Imagine facing a wardrobe filled with clothing options for a casual social gathering. Despite numerous choices, a sense of uncertainty arises regarding appropriate attire. Discontent with the existing wardrobe and style may emerge, indicating a need for sartorial reinvention. This experience is common, and many individuals have a similar stylistic impasse. If the preppy aesthetic appeals to you, it may offer a suitable solution.

This blog will illustrate the value of the preppy aesthetic and offer some tips for embracing it. You’ll even learn how WhatColors’ AI personal color analysis can help you build an elegant and versatile wardrobe to elevate your style without breaking the bank.

Table of Content

• What Is Preppy & Where It Came From

• 10 Key Elements of A Preppy Look

• 8 Do’s and Don’ts of Preppy Style

• What Does Preppy Style Mean Now?

• How to Get the Preppy Look for Kids

• The Preppy Gentleman's Style & Clothes Primer

• Ultimate Women’s Preppy Style Guide for All Occasions

• Perfecting the Preppy Style Over 50

• 15 Back-to-School Items You Need to Nail the Modern Preppy Aesthetic

• 20 Preppy Brands to Elevate Your Style

• Try AI Personal Color Analysis For Free Today
  
  

What Is Preppy & Where It Came From

Preppy is a style of dress inspired by the clothing worn by the Ivy League students of the 1950s and '60s. It's characterized by a classic, clean-cut look, emphasizing timeless pieces that never go out of style. Typical preppy clothing includes:

• Polo shirts

• Chinos

• Blazers

• Cable knit sweaters

• Boat shoes
  
  

The Rise of Preppy Style

The earliest iteration of the Ivy League look took shape on the campus of Princeton in between the First and Second World Wars. With imposing gothic architecture and high iron gates, located in what was then referred to as the swamp of rural New Jersey, its appearance wasn’t dissimilar to that of a British country pile. Its relative isolation allowed its predominantly male, white, and Protestant students to experiment with the sporting and high-society clothing popular across the pond: 

• Tweed jackets

• Polo coats 

• Button-down shirts 
  
  

Princeton's Preppy Pedigree

In her article, The Inter-War Years and the Birth of the Ivy Style, Patricia Mears of New York’s Museum at Fashion Institute of Technology wrote, “No other university defined Ivy Style as fervently and as beautifully as Princeton in the 1920s and 1930s. More than the other Ivies, Princeton was the keenest advocate of WASP elitism.”

“The insularity of the campus, the self-regulating and elite nature of the student body, the importance of extracurricular activities such as sports, and the widespread acceptance of sportswear shaped an environment where clothing took on heightened meaning,” adds author and fashion historian Deirdre Clemente.

Ivy Style Goes Mainstream

“The strict social hierarchy created and enforced by students for students did much to create a standard style for the public image of the Princeton man. The image was heralded and endorsed by mass-circulated magazines and clothing manufacturers who borrowed the University’s name for everything from shoes to shirt collars.” 

Brooks Brothers and J Press, early arbiters of Ivy style, opened stores around Princeton, Yale, and Harvard, selling:

• Boxy, lightly structured sack suits

• Unpleated flannel trousers

• Brushed Shetland knitwear

• Repp stripe ties
  
  

Ivy Style Evolves

Chipp in New York faded away before being brought back in a zombified form by Rowing Blazers a few years ago. Bass Weejun penny loafers became the de facto shoe of the campus, often worn without socks. 

Colleges were seen as incubators of impeccable style. A 1933 Apparel Arts article stated, “The American University man is justly famed for representing, as a class, a high standard of excellence impersonal appearance. Much of the secret of this distinction lies in the fact that the first thing the freshman learns is the importance of never looking ‘dressed up,’ while always looking well dressed.”

The Globalization of Preppy Style

In 1965, a group of style aficionados from Japan traveled to America to capture the Ivy League student in his natural habitat. The group included Toshiyuki Kurosu, Teruyoshi Hayashida, Hajime (Paul) Hasegawa, and Shosuke Ishizu, who founded the original Japanese Ivy-inspired brand Van Jacket. The result was Take Ivy—a book (a bible in certain circles) and accompanying film that captured vigorous-looking students striding around on campus wearing:

• Untucked OCBDs

• Bermuda shorts and sweatshirts

• Bass Weejuns with no socks 

• Unstructured tweed jackets
  
  

Ivy Style Reimagined

The Japanese fantasy of American Ivy was, in large part, just that. As Kurosu noted to writer and Japanese culture expert W David Marx, much of the book and film were staged: “Most students acted like they were completely disinterested in fashion, even if they looked like they cared. They didn’t seem proud of being stylish. They would just say to us dismissively, ‘I just came here to study. I don’t care what I wear.’”

As Ivy spread from the cozy campuses of the elite into the wider consciousness, it was utilized in new and exciting ways by demographics that had often been excluded from the conversation. In his 2021 book, Black Ivy: A Revolt in Style, Jason Jules discusses how the most notable black jazz musicians, writers and activists of that period were able to put their twist on Ivy during a time of significant social and political upheaval: Miles Davis, Robbie Coltrane, James Baldwin and Malcolm X were, as Jules calls it:

• Dressing as an act of subterfuge

• Mixing repp silk ties with denim workwear

• Button-down shirts with sunglasses

• Dressing as equals to their white counterparts
  
  

Ivy Style as Rebellion

“One of the key goals was to be visible and to challenge the clichés and perceptions of mainstream America. Wearing those clothes was a direct challenge to those negative assumptions.”

Preppy Style in Contemporary Culture

You can trace a thread from those early adopters to contemporary style icons like André 3000 and Tyler, the Creator, famous black men taking something typically seen as white golf or skateboarding or wearing a pearl necklace and skewering it with confidence and a sense of humor. Ivy gives way to prep, a term with more loaded connotations (Brooks Brothers famously disliked being referred to as prep).

Prep: Ivy's Playful Cousin

It was brighter and looser than its predecessor, retaining the same aesthetic language but more open to derision. Where Ivy was a way of living, prep was often seen as costume—the Yuppie-core of Bret Easton Ellis and Wall Street; books like The Official Preppy Handbook, and the satirical 1979 Are You a Preppie? posted by Tom Shadyac. One of its lines reads: Do you dress in a way that attracts women to other men?


Key items were:

• Deck shoes

• Washed denim

• Pastel polo shirts

• Khaki pants

• Signet rings

• Navy blazers
  
  

“Preppy is postmodern Ivy League,” the author and authority G Bruce Boyer told Ivy Style. “It’s a more conscious thing. Even the jazz guys who played on campuses consciously copied and modified that look. And Ralph Lauren made a fetish out of much of that stuff.”

Ralph Lauren: Prep's Visionary

Despite starting in 1967 by selling ties out of a drawer in the Empire State Building, Ralph Lauren, born Ralph Lifshitz, has proven to be the one who foresaw and mapped out the modern scene of lifestyle and what we now see as prep. Brands like Drake’s (full disclosure, they are my employer), Aimé Leon Dore, Thom Browne, P Johnson, and Rowing Blazers have all built on Ralph's foundations. 

Ralph Lauren's Legacy

Buy this; wear it here. Ralph the cowboy, Ralph the city slicker, Ralph the family man, Ralph, the beaming recipient of an award wearing an immaculate tuxedo.

“Brooks Brothers was the foundation, and I revived it,” Lauren, who started at the company before founding his eponymous brand, said in a 1985 interview with New York Magazine. “What Brooks Brothers used to be when they were great—that was what I went after, what I love, which is a lifestyle.

Ivy Style: Timeless Appeal

Men with a lot of money would go into Brooks Brothers to buy shirts and say, ‘Give me three white, three blue, and three pink,’ and they’d walk out. They’d do it every year, year in and out. They weren’t interested in what the latest this or the latest that was. I recognized a certain mentality and security about them. Working there was like going to an Ivy League school; there was an ‘in-ness,’ a quiet ‘in-ness’ about that kind of place.”

From square-jawed Princeton boys to the Lo Lifes smashing in windows on Madison Avenue, the story of Ivy and prep is modern America, a sense of opportunity and constant reinvention. You can be whoever you want to be if you wear the right clothes.

Related Reading

• Preppy Clothes
• Preppy Outfits
• Preppy Style
• Preppy Girl
• Preppy Photos
• Preppy Pictures
• Preppy Room
• Preppy Stuff
• Preppy Nails
• Preppy Bedroom

10 Key Elements of A Preppy Look

1. Wearing Classic and Traditional Clothing

The preppy style emphasizes classic and traditional clothing that exudes sophistication and elegance. These pieces will stand the test of time and never go out of style. They include:

• Well-tailored blazers

• Crisp white button-down shirts

• Timeless khaki pants
  
  

These versatile items can be dressed up or down for any occasion. Regarding preppy style, it’s also essential to opt for timeless designs. Instead of following fleeting trends, preppy fashionistas choose pieces that have a timeless appeal. Think:

• A-line skirts

• Pleated trousers

• Tailored dresses
  
  

Fit is Everything

These designs flatter various body types and exude a sense of refined elegance synonymous with the preppy style. Choosing tailored and well-fitted clothing is essential in achieving a polished, preppy look. Whether a custom-made suit or a perfectly hemmed skirt, well-fitted clothing enhances your overall appearance and gives off an aura of confidence and sophistication. 

Investing in a good tailor can make all the difference, ensuring that your clothes fit you like a glove and flatter your body shape. It’s not just about your clothes but how they fit you, that truly sets the preppy style apart.

2. Incorporating Bold and Vibrant Colors

While preppy style is often associated with neutral colors such as navy, white, and beige, don’t be afraid to incorporate bold and vibrant hues into your outfits. Adding pops of color can be a great way to inject personality and energy into your preppy ensemble. Opt for bright shades such as coral, lemon yellow, or cobalt blue to make a statement. Pair a vibrant-colored blouse with a classic navy skirt or trousers for a fresh and modern twist. Experimenting with color blocking is another fun way to incorporate bold colors into your preppy wardrobe. Pair a bright pink blazer with emerald green pants or a yellow blouse with a royal blue skirt.

Color Pop

The key is to find complementary colors that create a visually striking yet harmonious outfit. Accessorizing with colorful accessories is another great way to incorporate vibrant colors into your preppy style. Choose statement accessories such as:

• A bold red handbag

• A turquoise belt

• Colorful patterned scarves
  
  

These accessories can add a touch of playfulness to your outfit and instantly elevate your look.

3. Embracing a Preppy Wardrobe

A preppy wardrobe is characterized by its classic and timeless pieces. Embracing a preppy wardrobe means incorporating key items synonymous with the preppy style. Start by wearing:

• Polo shirts

• Button-downs
  
  

These classic tops are a preppy staple and can be dressed up or down depending on the occasion. Pair a polo shirt with chinos for a casual yet put-together look, or wear a crisp button-down shirt tucked into a skirt or trousers for a more formal outfit. Choosing cardigans and sweaters is another must-have for a preppy wardrobe. 

Layer Up, Level Up

These cozy knits can be layered over shirts or dresses, adding a touch of warmth and sophistication to your outfit. Opt for classic colors such as navy, cream, or camel for a timeless look. Adding blazers and vests to your outfits is a great way to elevate your preppy style instantly. A well-tailored blazer can transform any outfit, making it look more polished. Pair it with a button-down shirt, khaki pants, and loafers for a quintessential preppy ensemble. 

Conversely, vests can add a touch of preppy sophistication to a dress or blouse. Layer a vest over a white button-down shirt and pair it with a skirt or trousers for a chic and professional look.

4. Showing Off Sophisticated and Preppy Footwear

Footwear is an essential element of preppy style fashion, and several options can help you achieve a sophisticated and polished look. For a classic preppy footwear choice, opt for boat shoes and loafers. These slip-on shoes are comfortable and exude an air of casual elegance. Pair them with chinos, Bermuda shorts, or dresses for a preppy and effortless look. 

Footwear Finish

Oxford shoes and ballet flats are another excellent option for preppy footwear. Oxford shoes are known for their timeless appeal and can easily be styled with trousers or skirts for a sophisticated look. Ballet flats, on the other hand, are both comfortable and chic. Opt for pairs in neutral colors such as black or nude to ensure versatility, and pair them with your favorite preppy outfits. 

Wearing leather boots is another way to achieve a polished preppy look. Opt for knee-high or ankle boots in classic colors such as black or brown. These boots can instantly elevate any outfit, whether a skirt, dress or a pair of jeans. The sleek and polished look of leather boots adds an element of sophistication to your preppy ensemble.

5. Accessorizing with Preppy Style Details

Accessories are crucial in completing a preppy look and adding those finishing touches. Pay attention to preppy details that elevate your outfit and showcase your style. Adding pearl jewelry is a classic preppy touch. Whether it’s a string of pearls, pearl earrings, or a pearl bracelet, these timeless pieces instantly add elegance and sophistication to any outfit. 

Pair them with a button-down shirt, a tailored blazer, or a classic dress for a refined and feminine look. Wearing belts with statement buckles is another way to accessorize with preppy details. Opt for belts in navy, red, or brown colors, and choose buckles with fun designs or motifs like anchors or equestrian motifs.

Accessorize Away

These belts add a pop of color and showcase your preppy style and attention to detail. Sporting preppy watches or bracelets are a great way to add a touch of sophistication to your outfit. Opt for classic watch styles with leather straps in brown or black. 

Choose bracelets made with nautical-inspired ropes or colorful beads. These accessories will effortlessly complement your preppy wardrobe and add a subtle yet stylish touch to your overall look.

6. Opting for Classic Preppy Style Patterns

Patterns are a fun and unmistakable element of preppy style fashion. Incorporating classic preppy patterns into your wardrobe is a great way to showcase your love for this timeless style. Wearing stripes and gingham is a quintessential preppy choice. Whether it’s a striped shirt, a gingham dress, or a pair of patterned pants, these prints instantly add sophistication and classic charm to your outfit. 

Preppy Polish

Opt for classic color combinations such as navy and white or red and white for a timeless look. Another way to incorporate classic preppy patterns is to choose polka dots and tartan. Polka dots add a touch of playfulness and whimsy, while tartan showcases a sense of tradition and heritage. 

Wear a polka dot blouse with a skirt or trousers or a tartan blazer or skirt for a statement-making look. Incorporating houndstooth and plaid is another way to embrace classic preppy patterns. These patterns are known for their timeless appeal and can be styled in various ways. Choose a houndstooth blazer, a plaid skirt, or a pair of patterned pants for a chic and preppy look.

7. Maintaining a Well-Groomed Appearance

Preppy style fashion goes hand in hand with a well-groomed appearance. Paying attention to details such as hair, nails, and personal hygiene is essential in achieving a polished, preppy look. Keeping hair well-styled and neat is a crucial aspect of preppy style. Opt for hairstyles that are:

• Sleek

• Sophisticated

• Requiring minimal fuss
  
  

Grooming Matters

Whether you choose a classic bob, a polished ponytail, or a chic bun, the key is to ensure that your hair looks well-maintained and put-together. Consider investing in quality hair products and regularly visit a trusted hairstylist to keep your locks looking their best. Maintaining clean and manicured nails is another important aspect of preppy-style fashion. 

Opt for classic nail colors like:

• Nude

• Pale pink

• French manicure
  
  

Hygiene Essentials

Ensure your nails are well-shaped and free from chipped polish or rough edges. Regularly moisturize your hands and keep your nails clean and tidy for a polished look. Personal hygiene is essential in achieving a well-groomed appearance. 

Regular showering, using deodorant, and practicing good oral hygiene are essential yet crucial aspects of personal care. Wearing clean, well-pressed clothes free from wrinkles or stains is also important in maintaining a polished, preppy look.

8. Adopting Preppy Style Hairstyles

Your hairstyle reflects your style, and adopting preppy hairstyles is a great way to enhance your overall preppy look. Sporting a neat and polished hairstyle is key. Opt for hairstyles that are:

• Sleek

• Elegant

• Timeless
  
  

Hair Flair

Consider classic updos such as:

• A French twist

• A chignon

• A sleek low bun
  
  

These hairstyles instantly add a touch of sophistication and will effortlessly complement your preppy wardrobe. Wearing hair accessories such as headbands or ribbons is another way to embrace preppy hairstyles. Choose headbands in classic patterns such as polka dots or stripes or a ribbon tied in a neat bow. 

Effortless Waves

These accessories keep your hair in place and add a touch of preppy chicness to your overall look. Another preppy hairstyle option is styling your hair in loose and flowing waves. Opt for soft curls or beachy waves that are effortlessly stylish. Pair this hairstyle with a classic outfit, and exude an effortless elegance quintessential to preppy style fashion.

9. Choosing Preppy Style Bags and Accessories

Bags and accessories are the finishing touches that complete a preppy look. Choosing the suitable bags and accessories can take your preppy style to the next level. Opt for structured leather handbags for a classic and sophisticated choice. Choose bags in neutral shades such as:

• Black

• Brown

• Tan
  
  

These colors easily coordinate with a variety of outfits. A structured leather handbag instantly adds polish to any preppy ensemble and showcases your attention to detail. Preppy-inspired totes or backpacks are another option for those who prefer a more casual yet still preppy look.
 

Bag Charm

Opt for totes or backpacks in vibrant colors or classic patterns like stripes or gingham. These bags are practical and add a fun and playful touch to your preppy outfits. Accessorizing with matching wallets or clutches is essential for a coordinated and polished preppy look. 

Choose wallets or clutches that match your handbag or complement your outfit. These smaller accessories add a sense of cohesion to your overall look and showcase your attention to detail.

10. Embracing a Preppy Lifestyle

Preppy style fashion is not just about the clothes you wear but also about embracing a preppy lifestyle. It’s about embodying specific values and cultivating a polished and respectful demeanor. Participating in social and community activities is a key aspect of the preppy lifestyle. Whether volunteering, joining clubs or organizations, or attending social events, being involved in your community and engaging with others is a way to showcase your preppy values of:

• Camaraderie 

• Social responsibility
  
  

Graceful Conduct

Cultivating a polished and respectful demeanor is another important aspect of the preppy lifestyle. Politeness, good manners, and kindness are the foundations of preppy etiquette. Treat others respectfully, practice good table manners, and be mindful of your words and actions. A preppy lifestyle is about embracing elegance and sophistication in:

• Appearance 

• Behavior
  
  

Mindful Manners

Embracing the values of education and etiquette is a hallmark of the preppy lifestyle. Preppy fashionistas prioritize:

• Education 

• Continuous learning
  
  

Whether reading classic literature, staying informed about current events, or engaging in intellectual conversations, embracing a love for knowledge and education is essential to the preppy lifestyle. Practicing good etiquette in social situations, such as sending handwritten thank-you notes or practicing proper table manners, is a way to showcase your refined preppy style. 

Color Confidence

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

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

8 Do’s and Don’ts of Preppy Style

1. The Classics Are Key to Preppy Style

Classics are the most essential part of the preppy style. So, your wardrobe should include:

• Polo shirts

• Khaki pants

• Shift dresses
  
  

You can mix and match them with a touch of your personality. You can wear a blazer for sophistication or brightly colored Bermudas for a casual Monday.

2. Patterns Are Your Playground

Stripes, checks, and plaids are inevitable for preppy style. But don’t mix bald patterns with solid pieces. You shouldn’t go overboard.

3. Quality Basics Are Your New Investment Now 

Quality is always over quantity in preppy style—the golden rule! Because of that, invest in a well-made classic trench coat or a good piece of Mary Jane. Your preppy wardrobe will be timeless.

4. Use Accessories Wisely

Less is more when it comes to preppy accessories. Use them wisely! A statement belt, a sleek watch, or a headband can completely change your look. It is all about details, but don’t overdo it.

5. Don’t Use Too Many Logos

Elegance is your key! Don’t turn yourself into a billboard. Yes, it is one of your favorite preppy dress brands, but let your style speak for itself.

6. Tailoring Matters

A well-fitting outfit can make all the difference. It can be a classic blazer or a shift dress. Your clothing should hug you in all the right places. Wearing something too tight or oversized prevents you from having an elegant look.

7. Use Colors to Tell About Yourself

Colors are your palette now. Choose vibrant colors like mint green or a pop of coral to show your personality. A preppy look is also all about aesthetics, so bright hues are your weapon in your timeless wardrobe.

8. Too Many Trends Shouldn’t Be Mixed Up

Remember, we said the preppy look is always about timelessness. Trends are not timeless. So, don’t mix them up!

Related Reading

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

What Does Preppy Style Mean Now?

Preppy style has changed a lot over the years. It started with the wealthy elite of the 1950s. Think Ivy League students and their affluent parents, who liked to dress their kids in clean, classic styles that looked good for photographs. The kids wore these outfits to private school, where they were captured in pictures that made their way into the society pages of magazines like:

• Life

• Town & Country
  
  

The looks were all about status — a visual representation of wholesome American values. The color palettes were muted, emphasizing earth tones and pastels. The style was conservative and restrained, with little room for variation. In the 1980s, the preppy aesthetic went mainstream, largely thanks to pop culture.

Preppy Evolution

Characters like Blair Waldorf from Gossip Girl and Steff McKee from Pretty in Pink epitomized the look on television. At the same time, rappers like the Fresh Prince himself, Will Smith, infused a little color and personality into the style. Today, the preppy aesthetic is still evolving, but it's much more diverse and inclusive than it used to be. 

Prep-inspired looks can be found on the runways, in TikTok videos, and almost everywhere. With all the digital content at our fingertips, the preppy aesthetic has truly gone global.

What Is the New Definition of Preppy?

Preppy style today is all about bright colors, fun patterns, and a cheerful disposition. Whereas the looks used to be more serious and wealthy-looking, there's an element of fun and optimism that feels especially appropriate right now. 

From everything we can gather, the new definition of preppy is much more inclusive than it used to be, allowing for personal style and variation. "We are no longer in an era where you have to look like Blair Waldorf to identify with the aesthetic," says one expert. "Sure, you can rock the school uniform and the pastel color palette, but you can also mix in elements of cottagecore and even goth to create a unique style that reflects your personality."

Does the New Definition of Preppy Have a Negative Connotation?

For some, the term preppy conjures up negative stereotypes of rich, white kids who look down on others. Much like the term basic, it can also imply someone boring and conforming to societal standards. The new definition of preppy has changed, making it more approachable and less elitist. 

The new preppy is:

• Colorful

• Fun

• Exciting
  
  

While some may still hold on to old stereotypes, most people today simply embrace the aesthetic to express their individuality and personal style.

How to Get the Preppy Look for Kids

Chinos: The Preppy Essential for Boys

Chinos rank high on the list of preppy essentials for boys. These cotton blend pants are perfect for playtime as they’re:

• Stretchy

• Washable, but they also look great for smarter occasions
  
  

Chinos are easy to slip on for Christmas dinners or to wear as back-to-school trousers, and they are not boring old uniforms.

Button-Up Shirts: A Preppy Stapler

There’s something about a boy in a button-up shirt that’s just adorable. Whether you choose from check, gingham, plaid, or plain, worn open over a plain tee in early fall and, come winter, worn under a sweater, they will look brilliantly smart.

School Uniforms: The Unexpected Source of Preppy Style

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. And, because it’s schoolwear, you get all the added innovations (like non-iron shirts), so they’re super-durable and easy to wash.

Tartan: The Preppy Print

Whether it’s a shirt or skirt, tartan is a key addition to the preppy look. But there are a couple of rules to follow: don’t overdo it—one item is enough. Pair with neutrals, such as:

• Grey

• Black

• White
  
  

This skirt is a skort (a skirt panel at the front over shorts), making it brilliant for:

• Tree climbing

• Handstands
  
  

Polos: The Preppy Alternative to Tees

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. 

Top tip: If he lets you do up the top button, be extra smart.

Corduroy: A Timeless Preppy Fabric

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

Preppy Colour Palettes for Kids

Kids look brilliant in bright colors, but if you wish to keep the look classic, go for fall shades, such as:

• Navy

• Deep red

• Bottle green

• Mustard yellow 

• Rust
  
  

An added bonus: These colors don’t show up dirt as much.

Preppy Shoes: Get the Footwear Right

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 to be water-repellent, meaning they’ll stay smarter for longer.

Don’t Be Afraid of Sparkle

Glitter and sequins are too fabulous to leave out of the preppy look, so add in:

• Sparkly sneakers

• Bags

• Gloves 

• Scarves
  
  

If the outfit is simple and classic, like this fabulous spotted romper, adding some sparkle won’t stop the look from being smart.

Collegiate Style: A Cool Preppy Look for Kids

College-style baseball jackets, cardigans, and sneakers with contrasting trim work fantastically on kids. They never fail to look fantastic and give their outfits a smarter vibe.

Layering: The Key to a Smart Preppy Look

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 smart and adds detail. 

Pattern Play

Only have a pattern (check or stripe) on one of the layers and keep the block color neutral, such as:

• Blue

• Black

• Grey

• White
  
  

Layering means you can strip it off or add it on—very handy for active kids.

The Preppy Gentleman's Style & Clothes Primer

The preppy style is classic. It’s a timeless look that evokes images of well-heeled Northeastern American college students sporting:

• Boat shoes

• Blazers

• Pastel-colored polos
  
  

Ivy Roots

The style’s roots trace back to the Ivy League schools of the Northeast, where students from wealthy families would sport tailored, functional clothing on campus and during their leisure activities. Today, the term preppy is far looser and is regularly used in high schools across:

• North America 

• Parts of Europe
  
  

It still accurately describes the subculture of those who have adopted a manner of speech, vocabulary, dress, manners, and etiquette that reflects the traditions adopted from those historic upper-class Northeastern families.  

Prep for All

Nowadays, the prep style is far more accessible to a more fantastic range of people. Just as many other elements of fashion originating in wealthier wardrobes, preppy style icons such as:

• Salmon-pink trousers

• Cable knit sweaters,

• Humble button-down shirt
  
  

These styles have all become more affordable to a greater range of classic style enthusiasts.

Preppy Clothing Essentials

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

Preppy Style Jackets and Blazers: Classic Navy Blazer

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

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

Preppy Style Shirts: Polo Shirts & Oxford Button Down Shirts

Even if you don’t play polo, the brand made casual wear a near-universal addition to menswear! 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 trendy in prep culture and are often paired with the following:

• Iconic navy blazer

• A repp tie
  
  

Polo Powerhouse

Polo shirts, which can also be referred to as golf or tennis shirts, are a well-known staple in prep style. A casual and soft shirt with a collar, a placket, and usually two or three buttons can often feature a breast pocket. 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.

Preppy Style Trousers and Pants: Chinos, GTH (Go To Hell) Pants & Nantucket Reds

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

GTH (Go To Hell) Pants GTH pants take some serious getting used to. This style of its own 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

• A variety of other icons
  
  

Red Revolution

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

The red pants, shorts, shirts, hats, and other articles were originally distributed by Murray’s Toggery Shop in Nantucket and are guaranteed to fade to an almost rosy pink. They are traditionally pants, but today, they consist of an entire selection of clothing and accessories that are incredibly popular to the point of being legendary in Martha’s Vineyard, Cape Cod, and their birthplace, Nantucket.

Preppy Style Knitwear: Cable Knit Sweaters & Argyle Sweaters

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

Argyle Appeal

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

Preppy Style Footwear: Loafers & 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. 

Loafer Legacy

Loafers are typically worn without socks as casual shoes and, as such, are tied using leather boat shoelaces. Like boat shoes, loafers 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 slippers indoors. 

Traditionally, 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, and materials and occasionally feature tassels or decorations on the front of the shoe.

Preppy Style Outerwear: Barbour Wax Jacket 

Barbour wax jackets are extremely popular with Prep’s and 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.

Ultimate Women’s Preppy Style Guide for All Occasions

A Fresh Look at Preppy Style

The preppy style is defined by understated elegance and minimalist details that work for many upcoming occasions, from casual weekend brunches to sophisticated garden parties. As of late, creators and fashion figures alike are forgoing trendy styles and sporting crisp, understated ensembles brimming with:

• Smart knitwear

• Sharp suiting

• Clean button-downs

• Structured totes
  
  

These safer styles, which feature key pieces from this preppy style guide, are our stylist's most repeated thanks to their sleek style codes that transcend the ever-changing trend cycle.

Preppy Clothing Essentials

Several key pieces should be on your radar when building a preppy wardrobe. These classic items form the foundation of the aesthetic and can be mixed and matched to create a variety of stylish outfits. Let’s explore some of the must-have essentials:

The Navy Blazer: A Timeless Classic

The navy blazer is a quintessential staple that exudes sophistication and versatility. It can be dressed with a crisp button-down shirt and a skirt for a formal occasion or paired with jeans and a t-shirt for a casual look. This versatile piece is a must-have in any preppy wardrobe.

Polo Shirts: Sporty and Stylish 

Polo shirts are synonymous with this style. They perfectly balance casual and refined, making them suitable for various occasions. Opt for colors like:

• White

• Navy

• Pastels
  
  

Wear them with chinos or shorts for a preppy summer look.

Boat Shoes: Nautical Charm

Boat shoes are essential preppy footwear made by brands like Sperry. These shoes are comfortable and versatile, exuding a nautical charm that perfectly complements the aesthetic. Pair them with shorts, denim, or summer dresses for a relaxed yet polished look.

Button-Down Shirts: Crisp Essential

Button-down shirts are a cornerstone of preppy fashion. They deliver a clean and polished look that can be dressed up or down depending on the occasion. Opt for classic patterns like stripes or gingham, and pair them with jeans, a tennis skirt, or khaki pants for a timeless outfit.

Cable-Knit Sweaters: Cozy and Chic

Cable-knit sweaters are another staple of this style. They offer a cozy and chic look that is perfect for colder seasons. Layer them over button-down shirts or wear them on their own with jeans or skirts for a perfect preppy ensemble.

Trench Coat: Outerwear Elegance

A trench coat is a versatile outerwear piece that adds a touch of timeless elegance to any outfit. It is a perfect transition from spring to fall and can be worn over casual and formal attire. Opt for a neutral color palette like beige or navy for a fantastic look.

Khaki Pants: Classic and Versatile

A trench coat is a versatile outerwear piece that adds a touch of timeless elegance to any outfit. It is a perfect transition from spring to fall and can be worn over casual and formal attire. Opt for a neutral color palette like beige or navy for a fantastic look.

V-Neck Sweater: Sophisticated Layering

A v-neck sweater is a sophisticated layering piece that adds a touch of refinement to any outfit. It can be worn over a button-down shirt for a classic look or layered under a blazer for a business casual ensemble. Opt for neutral colors like navy, gray, or camel for an enduring appeal.

Oxford Shirts: Timeless Elegance

Oxford shirts are a preppy essential that will always be in style. These versatile pieces can be dressed up with a blazer or dressed down with jeans or shorts. Opt for colors like white, blue, or pink for a traditional look.

Pleated Skirt: Chic Look

A pleated skirt is synonymous with the preppy aesthetic. It’s a chic look perfect for different seasons. Pair it with an elegant blouse and cardigan for the ideal look.

Preppy Style Outfits for Various Occasions

For the Beach: Crisp Button-Up Shirt, Crochet Shirt & Flip-Flops

Is there anything preppier than a white button-down shirt? We think not, especially when it comes to beach-chic style. Crisp and clean, this tailored top adds instant polish to the laid-back pieces we gravitate toward for oceanside activities. 

Whether you choose a crochet skirt (which we love for summer 2024) or a pair of linen trousers, the white button-down shirt will give any beach ensemble that prep-and-polished feel. While we love minimal styles with pointed collars as our forever staples, versions with:

• Puffed sleeves

• Exaggerated cuffs

• Oversized silhouettes
  
  

For Lunch in the City: Tailored Trousers, Tank Top & Ballet Flats

Much like a white button-up shirt, a pair of well-tailored trousers is worth investing in to ensure any look has a preppy touch. Whether you choose flared, straight, cropped, or wide-leg (each works best for different body types), the style acts as a foundation for a polished look that can easily transition from lunch in the city to the office. 

During the summer, we love pairing the style with a tank top, thin belt, and ballet flats to lean into the preppy feel without worrying about overheating. Because the style is inherently versatile, you can also wear it in the winter with a crewneck sweater and closed-toe pumps.

For Window Shopping: Slip Dress & Ballet Flats

You may be sensing a theme here: The key to creating a preppy look is opting for elevated versions of the basics. The next critical component is an elevated slip dress that can be worn from day to night. If you’re wearing it for window shopping, sport the slinky dress with a pair of your go-to sandals, whether a classic flip-flop or a dad sandal, for that added edge to ensure you're comfortable while getting those steps in. 

Swap your sandals out at night for kitten heels, and tie a sweater around your shoulders for an equally preppy look.

For The Office: Coordinating Pantsuit & Loafers

Pantsuits are a hallmark of office style and feel incredibly preppy in oversized silhouettes and luxurious fabrics like silk and wool. The quintessential menswear staple is not only chic and work-appropriate but also versatile enough to mix and match with other items in your closet. But if you aim for a polished work uniform, you can’t go wrong with a coordinated pantsuit.

White sets are the ultimate summer staple, as they exude freshness and elegance. However, having several other colors in rotation—whether black, beige, or pops of color like maroon or navy—ensure your suits will transcend style trends and withstand the test of time. The finishing touch? A pair of classic loafers that are equally preppy and functional.

For Getting Those Steps In Baseball Cap & Sneakers

We get it: Sometimes, there's not enough time for Pilates or a run. Instead, there's only time for a breezy stroll, and with it comes a casual outfit you can wear around the neighborhood. Hence, sleek athleisure in stretchy jeans, a baseball cap, and some sporty trainers ticks all the boxes for preppy style. 

In that same vein, it’s crucial to keep yourself looking sporty-chic and comfortable. Baseball caps are the epitome of preppy style during these laid-back moments (and, of course, shield us from those nasty UV rays), and with a pair of trainers, they tie together a look that is both:

• Functional

• Polished
  
  

Discover Your Colors with WhatColors

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

Perfecting the Preppy Style Over 50

The preppy aesthetic has a long history of popularity, with roots in the 1900s. It first gained traction among Ivy League students and has since undergone numerous evolutions, becoming more inclusive and diverse with each iteration. 

While the style is often associated with youth, it can work for anyone and is especially adaptable for those over fifty. Preppy styles today embrace a cooler, more modern vibe, making them perfect for older adults seeking to express their individuality. 

15 Back-to-School Items You Need to Nail the Modern Preppy Aesthetic

Preppy fashion is back in a significant way among students. The aesthetic—short for preparatory—is particularly trendy right now, thanks to Miu Miu’s ultra-cropped cable knits and cultural touchstones like Euphoria. But while the look is having a moment, it’s never really lost its relevance.

After all, the preppy style has a formidable history. Think back to its most venerated icons: 

• A young Princess Diana, swathed in Sloane Ranger pearls and pie-crust collars

• Alicia Silverstone’s Cher Horowitz with her headbands, pleated skirts, and argyle cardigans

• Jackie Kennedy-Onassis in her collared shirts and sweaters, tied loosely around her shoulders. 

There’s a reason these ladies still hold such a stronghold on fashion today. Their looks exude a particular kind of wealth and privilege that will always be desirable.

The Modern Preppy Look

The preppy style is appealing because it’s gotten a severe modern refresh. For one, it’s much more diverse than it used to be. Today, anyone can dress like an Ivy League student, regardless of background or personal style. 

There’s also a lot more room for individual expression within the aesthetic; it’s no longer about looking like you just stepped off the campus of Harvard University but instead taking the classic staples and making them your own. Mix and match your preppy pieces with other styles, from goth to grunge to streetwear.

Essential Items for a Preppy Wardrobe

However, because of its formidable history, narrowing down the items you need to channel country club chic poses a challenge. So here, we’ve curated a list of all our favorite preppy clothing and accessories, from fundamentals like Ralph Lauren jumpers and baseball caps to tennis dresses and striped rugby knits. 

Scroll below to discover the staples; we guarantee you’ll dress like an Ivy League student in no time. 

1. Grey Double Pleats Midi Skirt

Every preppy wardrobe needs a pleated midi skirt. This Dunst design lands in the sweet spot between back to school and tennis round on a Sunday afternoon—exactly where every boat-shoe lover wants to be.

2. Stripe Rugby Knit

Preppy style and polos come hand in hand. This long-sleeved, striped rugby knit is a must-have. Tuck it into a flippy skirt and wear it with tube socks and loafers for the poshest effect.

3. Jersey Tennis Minidress

This is self-explanatory. You can look like Billie Jean King in this Tory Burch tennis dress. This is athleisure at its finest, and by that, we mean styling yourself like an athlete but being a woman of leisure.

4. Ruffled Exaggerated Collar Blouse

For the more contemporary preppy style acolyte looking for an out-of-the-box collared shirt, Ganni will undoubtedly have what you want.

5. Polo Ralph Lauren Fleece Crewneck Pullover

Polo Ralph Lauren and labels like Tommy Hilfiger and Brooks Brothers practically invented prep and preppy style. Wear their iconic Polo player and pony—the badge of all preppy fashionistas—in this versatile pullover.

6. Jane Debster Kassidy Loafer

Simple, durable, and Australian-made, these Jane Debster loafers are necessary.

7. New Era Casual Classic New York Yankees Baseball Cap

Pop this baseball cap on with a boxy blazer, white t-shirt, and jeans, and you’ll be ready to hit the town, Princess of Wales style.

8. Polo Ralph Lauren Julianna Cable Knit Cotton Crewneck Sweater

A cable-knit is a staple plucked straight from the official preppy handbook. Wear tucked into jeans or a checked skirt, or even better, drape over the shoulders and tie loosely at the front. It’s the I’m a little too warm after my stroll around The Hamptons look.

9. Sézane Betty Cardigan

It wouldn’t be a preppy wardrobe without nautical stripes. This sugar-sweet cardigan from Sézane is an excellent place to start, and it comes in an array of bright colors, too, should you fancy them.

10. Saks Potts Brown Venus Polo

This polo shirt from Scandi-label Saks Potts is as preppy as it gets. All you’re missing is a visor, gloves, and an equally well-dressed caddy. Peak preppy fashion.

11. Everlane Silky Cotton Relaxed Shir

Treat your collared shirts like T-shirts and own them in abundance. This Everlane design comes in a variety of neutrals and preppy-friendly stripes.

12. Tory Sport Performance Pleated Laser-Cut Stretch Tennis Skirt

This pleated mini skirt has built-in mesh shorts so you can look and live the preppy golfer’s lifestyle.

13. Reliquia Jewellery Nina Headband

A headband can prep-ify any outfit. This wider style from Reliquia Jewellery comes in various satin shades, but our favorite is this versatile olive.

14. New Balance 530-Unisex

These retro-style New Balance sneakers come in sandy beige to accessorize anything from your favorite jeans to your summer midi dress.

15. Adidas X Wales Bonner Argyle Knitted Ves

A knit vest, in argyle? That’s two boxes ticked off the prep school checklist.

Related Reading

• Preppy Colors
• Preppy Girl Aesthetic
• Preppy Skin Care
• Pink Preppy
• Aesthetic Preppy
• Preppy Definition
• Preppy Nail Colors
• Preppy Braces Colors
• Preppy Hair Colors
• What Colors Are Preppy
• Preppy Room Colors
• Pink Preppy Wallpaper
• Preppy Meaning
• Preppy Wallpaper Laptop
• Hailey Bieber Hair
• Cute Nail Inspo

20 Preppy Brands to Elevate Your Style

1. Barbour: The Classic British Brand for Outdoor Adventures

Whether you're planning a weekend of pheasant hunting or horseback riding, Barbour is the classic outerwear brand for such events. It's also perfect for outdoor fun, like pumpkin carving, walks in the forest, or jaunts to an apple orchard. 

Barbour makes top-quality outerwear you'll own for years to come. The jackets and vests come in classic shades and feature quilted nylon and water-resistant waxed cotton fabrics. Attention to detail includes coordinating plaid lining, warm pockets lined with moleskin, and many zippers, snaps, and vents for easy outdoor movement and comfort.

2. Burberry: The Quintessential Preppy Brand Fit for Royalty

If you want to dress like a queen, look no further than Burberry. Granted Royal Warrants by both Queen Elizabeth II and Prince Charles, this Bond Street fashion house has been a premier British brand since 1856. Burberry is known for its iconic trench coat, and the print initially used to line the coats is the Burberry Check. 

Burberry's quintessential plaid and top-quality construction have made the brand legendary. You can now wear Burberry as a full-clothier, including:

• Sunglasses

• Hats

• Coats

• Sweaters

• Handbags

• Leather goods

• Scarves
  
  

3. Draper James: Reese Witherspoon's Sweet Southern Brand

This sweet Southern brand is the brainchild of Legally Blondes' Reese Witherspoon. The preppy brand is filled with pretty dresses and accessories with a Southern twist. You'll want to fill your closet with the chambray, gingham, and magnolia-printed garments that make this brand even sweeter than your mint julep. Whether you are headed to a derby party or sipping sweet tea on the veranda, Draper James is a go-to brand for girls who want a preppy look.

4. Dudley Stephens: Eco-Conscious Fashions for the Prepster

If you're looking for an environmentally conscious preppy brand, consider Dudley Stephens. This female-owned company sources recycled fabrics to help keep plastics out of landfills and oceans. You'll love this brand if you want to look like you're ready to spend the day hitting the slopes or shopping boutiques in Vail, Aspen, or Park City. 

Their signature silhouette is the fleece turtleneck. It comes in a wide variety of colors and several lengths to flatter your figure

5. Hunter Boots: Preppy Wellies for All-Weather 

Keep your feet warm and dry no matter the weather in these waterproof, handcrafted, certified vegan boots from Hunter. Another iconic brand, Hunter, holds two Royal Warrants of Appointment to HM The Queen and HRH The Duke of Edinburgh.

Wellies are a favorite preppy wardrobe staple in many fun colors and styles. The photo above lists a few of our favorites, including the original tall boot, the Short boot, and the Chelsea boot.

6. Kate Spade: Whimsical, Colorful Accessories with a Preppy Flair

Kate Spade New York began in 1993 when Kate Brosnahan Spade couldn't find the useful bag she craved. Instead, she created her own and launched the brand with six versions of the Sam bag. Today, the brand features accessories including:

• Handbags

• Shoes

• Scarves

• Jewelry

• Clothes
  
  

7. J. Crew: Classic Preppy Styles for Everyone

For more than 35 years, J. Crew has been outfitting prepsters with classic looks at an affordable price. Their philosophy is: They make timeless clothes that last a lifetime…and pair them with of-the-moment styles season after season. 

This allows you to create a capsule wardrobe with essential pieces and mix in a few new items each season to keep it fresh and fun.

8. J. McLaughlin: Preppy Styles for Work, Play, and Beyond 

Founded in 1977, J. McLaughlin is a New York-based fashion brand focused on creating classic, quality pieces you'll have in your wardrobe for years to come. Whether looking for clothes for work, sport, or play, this preppy brand offers pieces to suit your needs with exclusive prints and excellent craftsmanship.

Preppy Pieces

You'll find:

• Swimwear

• Dresses

• Blouses

• Skirts

• Outerwear

• Sweaters
  
  

They also make preppy accessories, including shoes, beautiful wicker handbags, scarves, hats, belts, and sunglasses.

9. Jack Rogers: Preppy Sandals Inspired by Jackie O

Inspired by Jacqueline Kennedy Onassis, Jack Rogers makes perfect preppy footwear. The brand started with the Original Jacks, finely crafted sandals with a unique circular leather design. 

Jack Rogers Reign

Today, it has branched into many variations and colors of Jacks as well as:

• Other sandal styles

• Espadrilles

• Loafers

• Boots

• Slides

• Heels

• Wedges all with a preppy vibe
  
  

Jack Rogers makes embroidered sandals emblazoned with lobsters, anchors, ginger jars, and monograms. (PS. Preps love ANYTHING and EVERYTHING monogrammed!)

10. Kiel James Patrick: New England-Inspired Preppy Jewelry

If you want to add New England-inspired preppy jewelry to your wardrobe, look no further than Kiel James Patrick. The jewelry is designed and crafted in Rhode Island and invokes a sea-faring vibe of:

• Ropes

• Anchors

• Flags

• Knots
  
  

The brand has expanded into other accessories and clothing and remains a staple for preppies everywhere.

11. Lacoste: The Original Preppy Sports Brand 

Steeped in tennis history, Lacoste was founded by French tennis legend René Lacoste, a four-time international champion and the world’s best player from 1926 to 1927. Due to his tenacity on the court, he got the nickname the crocodile. 

He took the name to heart and started wearing crocodiles on his blazers and shirts. That launched a brand still known for its crocodile emblem and high-quality athleticwear that can be worn on and off the court.

12. Lands' End: The Classic Preppy Basics Brand

You'll be able to fill your closet with lots of preppy essential pieces to mix and match with Lands' End. This preppy brand started selling sailboat equipment to racing sailors and eventually grew into preppy apparel for all walks of life. Not only do they design the typical preppy garments such as dresses, shirts, skirts, shorts, swimwear, and outwear, but they also create other must-have apparel, including:

• Bras

• Underwear

• Activewear

• A large selection of women's plus-sizing
  
  

13. Lilly Pulitzer: Colorful Prints for the Preppy Lifestyle

Do you think a preppy wardrobe is full of plain, boring colors? Lilly Pulitzer will prove you wrong with a vibrant collection of patterns and prints that make any day sunny. Back in the late 1950s, Palm Beach socialite Lilly Pulitzer started a juice stand.

Lilly Pulitzer Legacy

Since the juices stained her clothes, she asked her dressmaker to create a dress to hide the stains. The result was a cotton print shift dress in citrus colors. The dresses quickly became more popular than the juice, and a brand was born. Today Lilly is still known for unique and colorful prints and figure-flattering silhouettes for the stylish, preppy girl. 

You'll find party-ready dresses, resort wear, stand-out work clothes, and activewear for:

• Golf

• Tennis

• Leisure
  
  

14. Ralph Lauren: The King of Preppy Fashion

Years ago, I saw Ralph Lauren interviewed. When he started in the fashion industry, he was Ralph Lifshitz, a New York men's ties salesman. He said he'd see all the wealthy New Yorkers heading to the Hamptons to party at their seaside mansions for the weekend. 

He envisioned their lives - attending polo matches, gala events, yachting, and lounging. So, he created clothes that fit that lifestyle and forever changed retail as we know it. Lauren was the first to create not just a brand but a complete brand lifestyle, including:

• Clothes

• Home goods

• Furniture
  
  

15. Sail to Sable: Classic Preppy Styles for the Nautical Lover

According to Sail to Sable's founder, Jennifer Stocker, the brand started with her original tunic dress design. That silhouette will forever be a part of the brand's signature pieces. They focus on easy-to-mix-and-match coordinating:

• Prints

• Bold colors

• Stripes
  
  

16. Southern Tide: Celebrating the American Lifestyle

Southern Tide products featured above: 

• Just Chillin Straw Sun Hat

• Natalia Tiered Navy Sun Dress

• Rheos Faris Sunglasses

• Southern Tide Beachside Tote Bag

• Skipjack Striped Key Fob

• Coral Leather Weekend Flipjacks (flipflops)
  
  

17. Talbots: Classic Styles for Every Woman

Talbots was started in 1947 by New Englanders Nancy and Rudy Talbot. Today, the brand focuses on modern classic style, creating versatile clothing you'll wear again and again that suits every area of your lifestyle. This preppy women's brand features size-inclusive clothing to fit 0-24.

18. Tory Burch: Boho Preppy Style with Class

Tory Burch is an American lifestyle brand that mixes classic style with bohemian elegance and embraces the spirit of adventure with:

• Character

• Color

• Beauty
  
  

The collection includes:

• Ready-to-wear shoes

• Handbags

• Accessories

• Watches

• Home

• Beauty
  
  

19. Tuckernuck: Nostalgic Styles for the Modern Prep 

Tuckernuck is named after a small island just off of Nantucket, MA. It's where the brand's founders, three friends, spent many happy summers together. 

The brand embodies its love of Nantucket and the nostalgic style represented there. It creates classic yet unique garments meant to suit the lifestyles of today's women.

20. Vineyard Vines: The King of Preppy Lifestyle Brands

Last on the list, but by no means least, is Vineyard Vines. It was started in 1998 by brothers Shep and Ian Murray, who desired to create a lifestyle brand with a relaxed, casual style reflecting life on Martha's Vineyard. 

Today, the brand sells men's, women's, and children's apparel with a focus on the preppy lifestyle, including:

• Fishing

• Golf

• Derby parties

• Enjoying life
  
  

Try AI Personal Color Analysis For Free Today

WhatColors helps you find what colors to wear based on your skin tone. Fet 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 ideal 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.