If you have admired the preppy style but needed clarification on its many definitions and wanted to understand it better before trying it yourself, you are not alone. Many people are drawn to preppy fashion's classic, polished looks but feel overwhelmed when defining the style and incorporating it into their wardrobes. The good news is that this guide will help you confidently understand the preppy definition and apply the look to your closet so you can embrace its timeless aesthetic. Whether it's the crisp, tailored pieces or the clean lines and bright colors, the preppy aesthetic embodies a sophisticated yet relaxed vibe that can easily elevate your everyday wardrobe.

One way to make the transition into preppy style easier is to use WhatColors’ AI personal color analysis app. This innovative tool will help you find your best colors and choose the right hues for your new preppy wardrobe, ensuring you look polished and stylish.

Table Of Contents

• What Is Preppy Definition & Meaning?

• The Essential Guide to Nailing the Preppy Look for Men

• How to Nail to the Preppy Aesthetic for Women

• 8 Do's and Don'ts of Preppy Style

• What Does Gen Z Mean by Preppy?

• 19 Preppy Nail Designs—From Plaid Accents to Sweater Designs

• How To Style Your Outfit The Preppy Way into Different Occasions

• 24 Designers You’ll Like if You Love Preppy Fashion

• Try AI Personal Color Analysis For Free Today

What Is Preppy Definition & Meaning?

The preppy style is more than just that; it is a style. Quite the contrary, preppy style is a nod to tradition, a celebration of the classics. Defined by clean lines, tailored fits, and a color palette that could make a rainbow blush with envy, preppy style is a lifestyle—a commitment to embracing both the polished and the playful. This style has its roots in the hallowed halls of Ivy League academia, where students rocked carefully put-together outfits that smoothly blended sophistication with a touch of rebellion. The campus became a runway, and the preppy look quickly transcended college gates, symbolizing timeless elegance.

Key Elements of Preppy Style

Now, let's talk about elements. Classic silhouettes? Check. Colors that evoke images of autumn leaves and ocean vistas? Double-check. Patterns that range from timeless plaids to crisp stripes? Triple-check. A preppy look is a harmonious blend of these elements, creating a visual symphony that's as pleasing to the eye as comfortable to wear. 

But it's not just about the clothes; it's a lifestyle. Preppy style and fashion are a mindset—a commitment to approaching life with grace and a twinkle in your eye. It's about taking that extra moment to ensure your bowtie is perfectly tied or choosing the boat shoes that can weather any storm, both metaphorical and literal. 

The Evolution of Preppy Style 

Here's the beauty of it all: preppy style is a chameleon. It's not confined to a gender or a generation. Men and women alike can embrace the crisp button-downs, the tailored blazers, and the pearls with equal enthusiasm. It's a style that transcends boundaries, inviting everyone to join the ranks of the effortlessly chic. For anyone who grew up in the late ’90s/early 2000s, being called “preppy” definitely drummed up a lot of specific images: crisp, pastel polos and pleated skirts, cable-knit sweaters around the shoulders, and trips to Nantucket with the family, for instance. 

It was the official look of the rich — the private-school-educated Blair Waldorfs of the world. Of course, not everyone who followed the “preppy” trend in real life was actually from some quaint New England town. Or rich, for that matter. As the aesthetic took over high schools across America, most teens achieved the “preppy” look by shopping at Abercrombie & Fitch and American Eagle. But these days, the definition of “preppy” seems to be expanding, and people on TikTok are trying to figure out what the “new preppy” looks like. 

The New Preppy Style 

In one video, @exfolikate responds to someone’s question about when and how the term “preppy” changed. “I am equally confused about this because this was preppy,” the TikToker says, pointing to a photo of herself in middle school. In it, she’s wearing a white polo top, a matching pleated skirt, and a string of pearls around her neck. The goal, she says, was “to look like a rich mother who just sits at a country club all day waiting for her tennis lesson.” “Let’s just call it Polocore,” the TikToker adds. 

But as many other TikToks are now showing, the “new preppy” is slightly different — in a hard-to-put-your-finger-on-it kinda way. Based on what’s being shared, Gen Z redefines the preppy look as less “New England country club” and more “relaxed and beachy Southern charm.” The outfits are colorful, the patterns and prints are bold, and the dresses are frilly. The occasional polo is still worn — and mini-skirts are still a thing — but the looks have a slightly more updated vibe that Gen Z loves. That said, not everyone on TikTok is getting the distinction. 

TikTok Users Get Confused 

“Wait, what is preppy now,” one person asked. “I’m confused,” added someone else. “It looks like everyone. So what are the different styles now?” “I prefer the old one,” said someone else, who was also a bit lost. “The new one confuses me idk why.” A lot of people found the old look preferable to the new one. “The old one was clean and professional,” one person said. “I love it.” 

Others defined the old preppy as “classy” and “timeless” than the new preppy. Some said the two were “giving new money vs. old money vibes,” while others felt the new preppy was just a recycled version of the “old Vsco” look. Whatever the case, the “new preppy” seems to be catching on. Only time will tell if it’ll stick around as long as the original look did.

Related Reading

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

The Essential Guide to Nailing the Preppy Look for Men

Wardrobe Staples For The Preppy Aesthetic

The preppy aesthetic has a strict uniform. You can make the style your own, but start with the critical pieces of the look: polo shirts, chinos, blazers, loafers, and the like. From there, explore the myriad ways to layer and combine these garments for texture, color, and pattern variation to achieve your desired visual. And don’t forget grooming. A clean, well-maintained appearance is essential to pulling off the preppy look. 

Stripes: The Preppy Pattern 

Whether it’s the collegiate stripes on a sports coat, the thin blue lines of a Breton, or the subtle pinstripe of a seersucker suit, the preppy uniformity of stripes can add a colorful, contrasting dimension to the look. The stripes originated in baseball, borrowed from British bankers of the early 19th century who wore certain styles of pinstripe suits to help identify which bank they worked for. A striped Oxford Cloth Button Down (or OCBD as they are known) can be a simple yet effective way to introduce the pattern into your wardrobe since you’re able to wear it with relaxed tailoring on the one hand or have the collar peeping out of a cotton sweatshirt on the other. Think pastel stripes in the summer, while in the cold months, opt for darker shades with more excellent contrast.

The Iconic Varsity Jacket 

The varsity jacket, aka ‘letterman jacket,’ is an icon of collegiate sports style, immortalized by Emilio Estevez in John Hughes’ cult classic The Breakfast Club. The tradition of awarding sporting high-achievers with letters (often the college's initials) to wear on their jackets harks back to the Harvard University baseball in 1865. 

However, back then, they were embroidered onto sweaters. The varsity jacket silhouette is typically that of the iconic MA-1 flight jacket with a ribbed elasticated collar and often with contrast-color sleeves. It’s an iconic piece of collegiate outerwear that combines well with the sportier elements of preppy style, and you’ll find no shortage of brands putting their stamp on the garment.

The Rugged Rugby Shirt 

A key piece in the preppy arsenal is the heavy cotton rugby shirt, with its requisite color-blocked panels and contrast soft-rolled white collar. Great as a way to dress down some separates, the rugby shirt is the perfect mixture of collegiate sports style and casual off-duty comfort. It’s also a great way to inject color into your look, adding a bold dimension to a navy blazer, chinos, or a corduroy suit. Typically constructed from heavyweight cotton, it’s an excellent year-round piece with myriad styling options.

The Essential OCBD 

The OCBD is like the glue that holds the preppy look together. With a soft-rolled collar and an even softer handle to the cloth, its charm is how it effortlessly dresses down tailoring and boosts knitwear. The button-down collar is a throwback to the original polo shirt, which British army officers in India devised to prevent the collar from flapping in their faces when they played polo. 

Pastel tones are de rigueur in the summer. They are casually worn with a French tuck into tailored shorts or chinos, the collar casually peeping out from a crewneck sweater. When worn with a suit or tie, the OCBD softens the formality of what could otherwise be a stuffy, uniform look.

Chinos: The Preppy Trouser 

Menswear has a lot to thank the military uniforms of history for, not least chinos. Developed initially from cotton twill for British and French soldiers in the mid-19th century, chinos have become a preppy staple, with the influx of military khaki in the 50s further cementing their status in preppy menswear. Cut with a straight leg and a reasonably low rise, the preppy style was and still is to wear chinos with a casual turn-up and loafers or boat shoes. They are the perfect casual trousers, being both lightweight and highly versatile.

Corduroy: A Textured Fabric 

Once the preserve of geography teachers (forever society’s style whipping boys), corduroy has shaken off its fusty reputation to become a non-negotiable fabric in today’s discerning wardrobes. It’s not hard to see why—corduroy’s textural quality is second to none, with those vertical wales providing an excellent tactile finish. Corduroy jackets, sports coats, and two-piece suits slide into the preppy aesthetic, pairing with an OCBD, crew-neck sweater, or polo shirt for a relaxed, tailored vibe.

Sports Coats: Not Just For Sports 

While it might not get the heart racing, the classic sports coat is integral to the preppy wardrobe. The style was initially created as a comfortable outer layer when participating in ‘sports’, namely plucking game birds from the sky. As a piece of hunting kit, it was typically made from hard-wearing tweed and was cut in a relaxed, unstructured style to allow freedom of movement. Flannel, houndstooth, and herringbone fabrics also became common in the sporting clubs of old, with many leaning on navy as a more cultured tone (bolstered by its nautical, military heritage). 

Whether you choose urbane navy or a more pastoral finish, the silhouette is the most essential feature. You want a softly tailored jacket with very little to no structure so that it drapes naturally. Navy works well contrasted with casual white trousers or chinos, while a brown houndstooth is well complemented with corduroy slacks or khaki pants.

Heritage Fabrics For Preppy Style 

One of the main reasons why preppy style has enjoyed unrivaled longevity is that it borrows classic menswear fabrics from the past and reinterprets them in a way that feels modern. Heritage cloths such as tweed, herringbone, and houndstooth, as well as patterns such as Madras check or Prince of Wales check, bring plenty of vintage sophistication to a look but can be given a creative appeal when matched with contemporary loungewear or streetwear. 

Think of a tweed sports coat casually thrown over a grey hoodie, loopback crew-neck sweater, and chinos. Or wear a bold Madras check shirt with a more understated charcoal flannel blazer. Heritage fabrics offer individuality and creativity while being far more versatile than you would think.

Loafers: The Preppy Shoe 

While polished black oxfords were the preference of their fathers, the original 1950s frat boys preferred the more casual approach of the loafer, most notably G.H. Bass’ iconic Weejuns. Whether penny loafer or tassel, the classic leather slip-on is a must-have in your preppy shoe rotation, pairing nicely with the more tailored aspects of the look. Today, you can be a bit edgier with your choice of loafer, opting for chunky soled varieties or fashion-forward styles with metalwork and embellishments. 

The once-lambasted white sock and loafer combo now seems to fly under the style radar, or you can opt to go sockless. Either way, the loafer is a stylish way to ground a seersucker suit or a pair of tailored shorts and an OCBD. Once again, it’s about complementing the polished leather of the loafers with a softer, more textural cloth in your outfit.

Nautical Influences 

Given that the Ivy League institutions are all dotted around the US East Coast, it’s no surprise that the preppy aesthetic comes with a healthy sea spray of nautical references, as many images of preppy poster boy JFK on his boat will testify. The key pieces then are heritage knits, such as Aran and cable-knit sweaters, alongside more contemporary takes on the classic lightweight windbreaker. 

The other great nautical item that fits perfectly with preppy style is the Breton top, that traditional long-sleeved cotton jersey with blue horizontal stripes. It is easy to pair with a Harrington jacket or blazer and adds a touch of Gallic maritime chic. Finish the look with Sperry’s boat shoes, a must for preppy summer looks.

Seersucker: The Summer Fabric 

Seersucker was popular with Ivy League students in the 1920s, and chief among them was Princeton’s preppy lot, which perhaps enjoyed the liberal connotations of that wrinkled, carefree finish. By the 1940s, Princeton’s boys’ preference for seersucker had lent it something of a sartorial halo, so much so that the Duke of Windsor wore a two-piece seersucker while on holiday in the Italian Riviera. While it’s commonly found with a pinstripe, many contemporary brands adopt it in block colors, trippier patterns, casualwear, and suiting.

The Shawl-Collar Cardigan 

Texture and tactility are always important when putting a look together, preppy or not. Traditional knits were and still are an integral part of preppy outerwear, in large part due to the nautical elements of the aesthetic. Hence, as mentioned above, the Aran and cable-knit jumpers are a great way to get the look. One piece of knitwear, however, jumps to the front of the preppy queue: the shawl-collar cardigan. 

Cardigans have that innately nerdy appeal, but adding the shawl collar brings a sophisticated formality to an otherwise relaxed garment. It’s still a very casual piece of knitwear, but the collar somehow raises it. Steve McQueen was often seen wearing one unbuttoned pair of jeans and bashed-up white sneakers, and you’d do well to take your styling cues from the King of Cool.

The Classic Polo Shirt 

Polo shirts were preppy fodder long before Ralph Lauren decided to embroider a polo player on his horse. However, credit where credit’s due – Mr. Lauren eternalized the association and made the polo shirt preppy lore. Can a man own enough polo shirts? Probably not. From cotton pique to knitted merino styles, the polo can take on sporty casual vibes and high-end luxury. Easy to style, opt for classic white or pastel tones worn beneath a simple crew-neck sweater and finished with a lightweight sports coat, chinos, and loafers. As close as you’ll come to an Ivy League uniform.

Technical Pieces For The Preppy Aesthetic 

Harking back to the East Coast predilection for sailing style, more technical fabrics have infiltrated the modern preppy aesthetic in recent years in the form of windbreaker jackets, technical blousons, and gilets. Aside from their apparent weatherproof functionality, these garments offer a nice textural contrast to natural fibers and juxtapose the more tailored aspects of preppy style with a sporting, outdoorsy aesthetic. A technical hooded jacket layered above an OCBD Merino sweater with straight-leg chinos and a pair of Sperrys is about as off-duty preppy as possible. 

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

How to Nail to the Preppy Aesthetic for Women

Preppy Fashion Essentials: Building a Classy Wardrobe

To nail the preppy aesthetic, you’ll want to start by building a wardrobe of classic pieces. Think button-down shirts, pleated skirts, blazers, and cardigans. Nailing preppy outfits and style is all about wearing these timeless, raised staples and channeling that “Old Money” look that TikTok loves so much. You don’t have to go full schoolgirl either — preppy pieces can be incorporated into super comfy outfits with a street-style twist. Varsity jackets, plaid mini skirts, neckties, sweater vests, and navy stripes are just a few options while exploring the preppy aesthetic. 

Proud Monograms: The Preppy Detail You Need  

Your average pullover sweatshirt transforms into a varsity look with one letter. Collegiate font patches are the ultimate preppy accessory.  

Cher Horowitz-Inspired Plaid  

Do Cher proud in a yellow mini straight out of the movie Clueless. Style it with a graphic knit to bring this '90s favorite into 2022.  

Vintage-y Cable Knit  

The combo of a red cable knit sweater and jeans is an easy, preppy outfit to pull off. Grunge down the look with Docs and a trendy shoulder bag.  

Cool in Crimson  

Layer a crisp white button-down under a logo t-shirt and add a pop of color with cherry red accessories. Preppy fashion never looked so cool.  

Trouser Shorts  

When temps get too high for full-on wool trousers, take notes from Barbie Ferreira, who styled long plaid shorts with a super relaxed button-down and choker for an updated prep look.  

Sweater (Vest) Weather  

Layering a sweater vest over a preppy button-down is perfect when you want to wear leggings without looking too fashionable.  

Preppy Prints Turned Cozy  

Trousers aren't just for internships and interviews -- they'll pair perfectly with your fluffiest, coziest cardigan, balancing out the look for a laid-back, preppy vibe.  

Plaid on Plaid  

Feel free to wear a monochrome look with prints. Hailey Bieber knows that plaid is neutral in classic shades like grey, black, or white.  

Belts, Caps, and Bags  

Accessories can make or break your preppy outfit. Classic bags, leather belts (for pants or dresses, of course), and cabby hats will take any ensemble to the next level. 
 

Gothic Peacoat  

This outfit is proof that preppy style can take on any vibe—even Victorian goth. Pair preppy items, like a peacoat that you'll wear for years, with edgy details, like these leather over-the-knee boots.  

Varsity Jacket  

Sift through your local thrift store (or raid your dad's closet) for a retro letterman jacket that gives off all the preppy feels. Pair it with a vintage concert tee and pants.  

Nautical Cardigan  

This is the ultimate preppy outfit. An oversized stripe-trim cardigan adds effortless elegance to a white tee and jeans. Keep accessories low-key so the sweater steals the show.  

Clean White Turtleneck  

A fitted white turtleneck is a tried-and-true preppy favorite. You can layer it under your favorite sweater, tuck it into high-waisted jeans, or double down on preppy vibes with a nautical striped skirt.  

Updated Penny Loafers  

Make your classic penny loafers feel fashionable with cropped jeans and cute striped socks. Adding a pair of black slip-on loafers instantly transforms any outfit into a preppy one.  

A Classic Varsity Sweater  

Nothing says "preppy" like a classic Lacoste varsity knit. Wear your oversized with slim joggers or wear skinny trousers and boots.

8 Do's and Don'ts of Preppy Style

1. Step Up to the Classics

When it comes to preppy fashion, classics are your best friends. Embrace the enduring charm of polo shirts, khaki pants, and shift dresses. These pieces are the backbone of preppy style, and you can mix and match them endlessly to create refined and laid-back outfits.

2. Avoid Overdoing the Logos

We get it – you love your favorite brands. But in the preppy world, subtlety is key. Avoid drowning yourself in logos from head to toe. Opt for understated elegance rather than turning into a walking billboard. Let your style speak for itself without shouting brand names.

3. Play with Patterns

Preppy fashion is the perfect playground for patterns. Stripes, checks, and plaids are your pals. Mix them up, but remember to balance bold patterns with solid pieces to avoid going overboard. It's all about finding that sweet spot between lively and refined.

4. Tailoring Matters!

A well-fitted garment can make all the difference. Whether it's a blazer, a pair of chinos, or a sundress, ensure your clothing hugs you in all the right places. Avoid drowning in oversized pieces or squeezing into something too tight. Tailoring is the secret weapon of the preppy elite.

5. Invest in Quality Basics

Quality over quantity, my friends. Invest in pieces that stand the test of time. A well-made blazer or a classic trench coat isn't just a purchase; it's a lifelong commitment to looking fabulous. Build your preppy wardrobe with pieces that can weather both trends and seasons.

6. Don't Shy Away from Colour

Preppy fashion is all about aesthetics, and color is your palette. Don't be afraid to infuse your wardrobe with bright hues. Whether it's a pop of coral or a splash of mint green, color adds personality to your preppy canvas.

7. Incorporate Accessories Thoughtfully

Accessories are the exclamation point to your preppy sentence. A sleek watch, a statement belt, or a tasteful headband can boost your look. Just remember, it's about the details, not the excess. Less is often more in the preppy playbook.

8. Don't Mix Too Many Trends

Preppy fashion has a rhythm, so avoid catching up on every passing trend. While it's fun to experiment, too many trends in one outfit can lead to a style cacophony. Stick to the timeless elements and sprinkle in trends sparingly.

Related Reading

• How to Be Preppy
• Preppy Outfit Ideas
• 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 Dresses

What Does Gen Z Mean by Preppy?

The term "preppy" has undergone a significant transformation in recent years. Once associated with a specific group of upper-class kids, especially those who attended elite schools, the preppy aesthetic today is much less exclusive. While it still draws from classic styles and designs, especially those popularized by the Ivy League, the modern take is more colorful, relaxed, and inclusive. Today’s preppy incorporates a range of trendy styles, and it’s not uncommon for a “preppy” outfit to include pieces from contemporary brands like Abercrombie & Fitch and Hollister. 

Gen Z’s New Definition of Preppy

Gen Z has taken to TikTok to explain their revamped definition of “preppy.” In a viral video, a group of young girls described the aesthetic as “fun and colorful,” “exciting and very girly,” and “stylish and comfy.” Though it’s easy to be perplexed by this new definition, the changes aren’t too surprising. As with any trend, new generations will adapt styles to fit their culture and preferences. 

According to Bark, a company that tracks teen social media trends, “preppy” is now used to describe a colorful, cheerful aesthetic that evokes notions of wealth and privilege. While the slang term “basic” describes someone perceived as boring, preppy conveys simplicity or predictability. The modern look resembles what the previous generation would have called the “rich girl” style. 

 Is "Preppy" an Insult? 

Like other fashion trends, many embrace the preppy look, while others find it unappealing. "Today, a girl walked up to me, and she said that my fit (outfit) was so 'Preppy Nation.' That I was looking preppy," said Mr. Lindsay in another TikTok video. Lindsay gestured to the Christmas sweater he was wearing, explaining, "This does not fall into my definition of preppy." He added, "Now, I've heard it used as both kind of an insult like -- 'Oh my gosh, that's so preppy' or 'That's Preppy Nation'" he said. "But I also hear them using it as like, a compliment: 'Oh, that fit is Preppy Nation' or 'Oh, it's preppy in here.'" 

19 Preppy Nail Designs—From Plaid Accents to Sweater Designs

Preppy nails are trending across social media, featuring the same designs and textures as prep apparel. Ahead, we've rounded up 20 preppy nail ideas to inspire your next manicure.  

1. Bold Blue Checkerboard

Checkerboard is another print that gives off preppy vibes. To make your mani stand out, opt for the pattern in a bold electric blue shade.  

2. Mismatched Mani 

Pairing cornflower blue and white nail polish creates a beautiful contrast. Meanwhile, the hand-painted flowers and checkerboards add a fun twist to this chic set.  

3. Green and Pink Patterns

This option is perfect for those who prefer short nails. The green and pink tiles give this set an upbeat, quirky feel.  

4. Red Plaid

Nothing says prep like a classic red manicure with a plaid accent nail. The swipes of glittery gold polish add a touch of glamour to the look.  

5. Burgundy French 

A burgundy French manicure is fitting for fall. The pumpkin orange and white stripes add a subtle touch of plaid to the look.  

6. Classic Checkerboard 

To keep things classic, stick with a traditional checkerboard print. It doesn't get much more cooler than a black-and-white manicure.  

7. Gold and White Stars 

Though a gold manicure is mesmerizing, you can easily make it more memorable with the right nail art. In this case, opt for giant white stars on the glittery base.  

8. Black Stars 

Channel your inner rockstar with this captivating set. The silver, glittery base and large black stars make this nail look electrifying.  

9. Red Plaid French 

Channel your inner schoolgirl with this red French manicure. Featuring a plaid accent nail and swipes of gold glitter, this set is sophisticated and stunning.  

10. Preppy Pink Chrome 

There are many ways to experiment with the preppy nail trend in a colorful way, as proven by this manicure. Mix pink chrome nails with vibrant checkerboard accents to create the most striking set.  

11. Gradient Sweater Nails 

Sweaters are part of every preppy look in the fall and winter. Use this set as inspiration and incorporate the texture of your favorite knitwear into your mani.  

12. Pink Sweater Nails

Here's another way to add texture to your French manicure. This long coffin set features cool pink tips decked out with sweater-inspired accents.  

13. White French 

Tips Since preppy style is timeless, you need an equally timeless manicure. A white French manicure perfectly fits this criteria.  

14. Refreshing Plaid 

This take on a plaid manicure incorporates unexpected shades like red, blue, and cream. Though plaid is such a popular print, this version offers something refreshing.  

15. Warm Tones 

Step into fall (and beyond) with a warm-toned manicure like this one. The mixture of brown, orange, and cream on the tips of each nail creates a gorgeous design.  

16. Denim Stripes 

Denim is a key part of many preppy outfits. This set features shades reminiscent of light and dark-wash jeans, making it an on-theme choice.  

17. Tortoise French Tips 

A tortoiseshell manicure is a perfectly preppy choice. Adding French tips to the marble-like design makes the set even more eye-catching.  

18. Pretty and Playful

 If you're feeling playful, try this manicure. It features fun colors—like baby pink and light blue—and whimsical designs, like cherries.  

19. Festive Argyle 

Argyle is another classic preppy print, and this set makes a strong case for incorporating it into your manicure. Here, shades of green, red, and silver come together to create a festive argyle mani.

How To Style Your Outfit The Preppy Way into Different Occasions

Casual Outings: Preppy Style for Low-Key Gatherings

For those laid-back weekends or coffee catch-ups, preppy fashion hits the sweet spot between casual and polished. Ladies, pair a crisp white button-down with tailored shorts or a knee-length skirt. Add a pop of color with your accessories, and you’re ready to take on the day. Gentlemen, opt for well-fitted chinos and a polo shirt for a look that effortlessly straddles casual and refined.

Business Casual: Preppy Style for the Office

Are you heading to the office but want to keep that preppy flair? Ladies, a tailored blazer over a button-down shirt and a pencil skirt is a competent move. Accessorize with a sleek watch and classic pumps. Gentlemen, boost your business casual game with a well-tailored suit in classic colors. Ditch the tie for a more relaxed feel while still exuding professionalism.

Outdoor Gatherings: Preppy Style for Warm-Weather Events

Preppy fashion is proper at home, whether it’s a garden party or a barbecue. Ladies, a floral dress paired with espadrilles or wedges is a winning combination. Don’t forget a sun hat for that extra touch of elegance. Gentlemen, embrace light-colored chinos or shorts with a crisp short-sleeved shirt. Boat shoes are the perfect finishing touch for an outdoor affair.

Formal Events: Can Preppy Style Go Formal? Yes!

Yes, preppy style can waltz into formal events with grace. Ladies, a well-tailored shift dress in a solid color or subtle pattern is a sophisticated choice. Add a string of pearls and heels, and you’re red carpet ready. Gentlemen, opt for a classic navy blazer paired with tailored trousers and a dress shirt. A silk tie or bowtie completes the ensemble, ensuring you stand out in the sea of suits.

Beachside Vibes: Preppy Looks for the Coast

If you find yourself by the coast, preppy fashion fits right in. Ladies, a breezy sundress in a nautical stripe or pastel hue paired with sandals is the epitome of seaside chic. Gentlemen, don a pair of well-fitted shorts with a lightweight button-down shirt—leave it untucked for that relaxed beach vibe. Boat shoes or stylish sandals are the go-to footwear for coastal cool.

Related Reading

• Preppy Colors
• Preppy Girl Aesthetic
• Preppy Skin Care
• Pink Preppy
• Aesthetic Preppy
• 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

24 Designers You’ll Like if You Love Preppy Fashion

1. Brooks Brothers: The Definition of Preppy Style

No one can deny that the Brooks Brothers is an American icon. Founded in 1818 in New York by Henry Sands Brooks, it introduced its first ready-to-wear suits in 1849. To give this some context, 1818 was the year the White House officially reopened after being burned in 1814 by the British in the War of 1812. Brooks Brothers has provided preppy clothing for the American elite (and beyond) ever since. Favored at the highest level by many US presidents, including most famously JFK, the brand is noted for its high-quality, timeless clothing. A true American institution. 

2. J.Crew: The Perennial Preppy Brand 

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 Aesthetic's Poster Child 

American designer Ralph Lauren (born Ralph Lifshitz) founded the Polo Ralph Lauren Corporation in 1967. In 1977, 10 years after the company was founded, it 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 Ralph Lauren was put on the map. Lauren 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 Preppy Chic 

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: Quiet Luxury and Italian Flair 

The quiet luxury movement borrows heavily from some of the understated but always sophisticated style of preppy fashion. 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: Italian 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 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 weaves in hoodies and sweats, giving a luxe touch to beautiful knitted fabrics. 

7. Pelota Sporting Clothiers: Preppy Athleisure 

British brand Pelota designs clothes for ‘Aprés Sport’, when 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: British Heritage Style 

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 the UK’s answer to Abercrombie & Fitch. 

9. Abercrombie & Fitch: An Iconic American Brand 

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 sporting and outdoor goods outfitter. 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 make its name in the first place: high-quality preppy basics that epitomize that laid-back California lifestyle. 

10. Tommy Hilfiger: Classic Americana with a Prep Twist 

The brand was founded by Thomas Jacob “Tommy” Hilfiger in 1985 and 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, since 2017, it has experienced a renaissance thanks to the revival of 1990s menswear. 

11. GANT: The Ivy League Look’s Godfather 

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, and button tab. Located near to Yale University, the US label played a major role in shaping the Ivy League Look as we know it today. 

12. Hackett: British Sophistication 

Hackett was founded in 1979 by Jeremy Hackett and Ashley Lloyd-Jennings from a stall on London’s Portobello Road selling used clothes. Hackett has become a stalwart of the new breed of fine British brands despite its humble beginnings. Today, you’ll find a wide-spanning range that runs the gamut from high-quality basics to bespoke tailoring. 

13. Drake’s: British Heritage 

Founded by Michael Drake in 1977 in London’s East End, Drake 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 recognized.A philosophy of producing timeless pieces with a relaxed elegance to exacting standards ran through Michael’s and the brand’s veins. It's 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. 

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 have 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 Brand 

Sperry is the original American brand of boat shoes, 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 various celebrities and presidents, including, again, JFK. 

16. Beams Plus: Japanese Ivy Style 

It’s an oft-repeated opinion in menswear circles that Japanese fashion didn’t just adopt preppy Americana – it perfected it. 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. L.L.Bean: Classic New England Prep 

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 vast: you’ll find smarter chinos and Oxford shirts among the camping gear and workwear. The label does a lot of classics but starts with its chamois shirts, logo tees, and quarter-zip tops. 

18. Lacoste: Preppy Sport Style 

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

19. Crew Clothing: British Heritage Sailor Style 

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 they also have 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 Preppy-Influenced Skate Brand 

Preppy fashion is so influential that it went 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 easy to wear. 

21. Ivy Ellis: Preppy Socks 

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

22. Vineyard Vines: The New England Preppy 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, and 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 made 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, and fisherman jumpers. With its collections still designed and made in Brittany, Armor-Lux brings a sophisticated, Gallic interpretation of the preppy style. 

24. Aime Leon Dore: Modern Prep 

With its lookbooks set in wood-paneled dorm rooms, cult New York label Aime Leon Dore wears its preppy influences proudly. The brand is one of a handful to have taken Ivy League style somewhere new in recent years. In the collection, you’ll find classic sportswear and more tailored preppy pieces like tweed jackets, 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. 

Try AI Personal Color Analysis For Free Today

The preppy aesthetic draws inspiration from the Ivy League schools of the Northeast. Think of it as the style of the well-off college kids you might spot in the campus library or at a sporting event. While they are undoubtedly intelligent and educated, these kids also know how to have a good time, and they dress for both occasions. The preppy aesthetic blends classic, traditional, and casual styles with bright colors, cheerful prints, and clean-cut and tailored silhouettes. 

Outfits are often layered and include feminine and masculine looks—a definite nostalgic element to the aesthetic draws from the 1920s through the 1990s. Of course, like any other style, the preppy aesthetic has evolved and continues to change today.  The look is less about specific pieces and more about the vibe and how it can be customized to fit your style.

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