When you picture a preppy-style outfit, you might envision a well-researched, intelligent character in a movie. But nerdy doesn’t have to mean boring. The preppy aesthetic is full of color, fun patterns, and personalization. It exudes a polished, put-together vibe while allowing for creativity. 

With preppy outfit ideas, you can enhance your style with an academic flair that always goes in fashion. You’ll always look confident and approachable when you nail this aesthetic like you just aced the exam. And this guide will give you the insights you need to achieve that clean-cut style effortlessly.

WhatColors' AI personal color analysis app can help you achieve your goals regarding preppy outfit ideas and nailing the preppy aesthetic. Analyzing your unique coloring enables you to discover the colors that best complement your natural features so you can create the most stunning outfits possible.

Table Of Contents

• What is Preppy Style?

• 14 Key Components of Preppy Fashion for Men

• 7 Wardrobe Essentials for the Preppy Woman

• How to Recreate the Preppy Style

• 33 Preppy Outfit Ideas for the Modern Woman

• 20 Preppy Outfit Ideas for Guys

• British Preppy Style for Men

• How To Dress Preppy On Any Budget

• 25 Preppy Clothing Brands You'll Be Shopping From All the Time 

• Try AI Personal Color Analysis For Free Today

What is Preppy Style?

Modern preppy style traces back to the collegiate rowing clubs of mid-19th-century England. Oarsmen wore brightly colored jackets to stand out to the crowds, who cheered them on at competitions. Later, students attending social functions would wear their rowing blazers in youthful sartorial rebellion. The jackets helped distinguish one rowing club from another, as they were often striped with different colors. 

Though the look caught on with Ivy League students across the Atlantic in the early 20th century, it wasn’t until the 1950s that the aesthetic took on a life of its own. By this time, it had been wrested away from Oxbridge and was creatively evolving in the elite corridors of the Ivy League. Preppy style symbolized moneyed, well-heeled upper-class privilege, and it was famously parodied in Lisa Birnbach’s seminal books, The Official Preppy Handbook and True Prep.

Sporting Goods and Rebellion: The Building Blocks of Preppy Style

The sporting influence was noticed in transatlantic translation, as pastimes such as polo, sailing, tennis, rugby, golf, and equestrianism all informed the preppy aesthetic. It was also, still, a mode of rebelliousness as students took elements of their fathers’ wardrobes and subverted them with a casual sports aesthetic that used bold color contrasts and patterns such as Madras check in what was perhaps a bid to differentiate themselves from the charcoal suits of the cubicle drones of white-collar America.

The Evolution of Preppy Style

The fact that preppy style hasn’t significantly changed since the 1950s tells you all you need to know about its timelessness. As one of the most referenced twentieth-century menswear movements, it has a popular culture to thank for much of its evolution over the decades, from JFK and Miles Davis in the 1950s to the Beastie Boys in the 1990s and Tyler the Creator today. 

In a sense, it has always been modern because it has incorporated elements of tailoring, vintage, and sportswear no matter what the decade, but more recently, it has had a contemporary shot in the arm thanks to specific brands like Noah and Rowing Blazers who have introduced a more urban aesthetic to the melting pot. 

Gucci, too, has been exploring a maximalist approach to preppy style since Alessandro Michele took charge as Creative Director in 2015, further propelling the look to a global audience. Its modernity, then, is all wrapped up in its diversity and versatility, giving us any number of ways to pull off the look.

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14 Key Components of Preppy Fashion for Men

1. Stripes Add a Playful Touch to Preppy Outfits

Stripes are a staple of the preppy aesthetic. 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 very effective way to introduce the pattern into your wardrobe. You can wear it with relaxed tailoring on the one hand or with 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.

2. The Classic Varsity Jacket for Preppy Style

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.

3. Rugged Rugby Shirts

A key piece in the preppy arsenal is the heavy cotton rugby shirt, with its requisite colour-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 even a corduroy suit. Typically constructed from heavyweight cotton, it’s an excellent year-round piece with myriad styling options.

4. The Oxford Cloth Button-Down: A Preppy Essential 

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 elevates 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 rigeur in the summer, casually worn with a French tuck into tailored shorts or chinos, the collar casually peeping out from a crewneck sweater. And when worn with a suit or tie, the OCBD softens the formality of what could otherwise be a stuffy, uniform look.

5. Straight-Leg Chinos for a Polished Look

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 (more of which are below). They are the perfect casual trousers, being both lightweight and highly versatile. Give the salmon pink variety a swerve unless you want to be a feature of parody menswear websites and instead stick to the classic khaki, off-white, and navy tones.

6. Corduroy for Texture

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 easily into the preppy aesthetic. Pair them with an OCBD, crew-neck sweater, or polo shirt for a relaxed, tailored vibe. Wider wales make more of a visual impact, while many brands make shirts and trousers in a subtle micro-wale corduroy. Either way, it’s an excellent option for introducing a textural contrast into your preppy look.

7. Sports Coats Add Class to Preppy Looks 

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 rustic finish, the silhouette is the most crucial 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.

8. Heritage Fabrics for Vintage Appeal 

One of the main reasons the preppy style has enjoyed unrivalled 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 and 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.

9. Shoes: Leather Loafers Are a Preppy Essential 

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 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 seem 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, 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.

10. Nautical Influences in Preppy Style 

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.

11. Seersucker for Summer Style 

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. Despite its slightly crumpled appearance, the suit was widely acknowledged as the pre-eminently tasteful summer fabric sported by only the most discerning stylish chaps. 

For a fabric whose roots were very much ingrained in the working class South, seersucker had, in a short space of time, become the choice of the rich and vivid (although that would again shift when jazz impresario Miles Davis wore seersucker on the cover of his live album At Newport 1958). While it’s commonly found with a pinstripe, many contemporary brands adopt it in block colors, trippier patterns, casualwear, and suiting.

12. Shawl-Collar Cardigans for Preppy Outfits 

Texture and tactility are always essential 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, the Aran above and cable-knit jumpers are great ways 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 elevates 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.

13. Polos Shirts: A Preppy Staple 

Polo shirts were preppy fodder long before Ralph Lauren decided to embroider a polo player on his horse. However, credit where it’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 finish off with a lightweight sports coat, chinos, and loafers. As close as you’ll come to an Ivy League uniform.

14. Technical Pieces for Layering 

Harking back to the East Coast predilection for sailing style, more technical fabrics have infiltrated the modern preppy aesthetic in recent years, such as 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.

7 Wardrobe Essentials for the Preppy Woman

1. The Preppy Shoe That Goes With Everything 

Loafers are a preppy essential for a reason: They are as versatile as they are timeless. This intelligent shoe looks polished yet approachable so you can wear it anywhere. Go for classic leather styles, like the GH Bass Weejuns or Gucci Jordaan loafers, or try an updated version with lug or platform soles. The best part? You can (and should) wear them with socks. The chunkier, the better. 

2. The Bag That Says I’m Not Trying Too Hard 

Lisa Birnbach, author of The Official Preppy Handbook, told BAZAAR, "Preppy is that Prada nylon bag sitting in the back of your closet for the last 10 years. Some newer bags are terrific but have quilting and pearls that are so fussy—and that is the antithesis of preppy." You heard it from the high priestess of preppiness herself, but it isn't more classic than a Prada re-edition. Nylon bags from Longchamp and Staud also possess the essential unfussy factor preppies love. 

3. The Preppy Flat That Goes With Everything 

Ballet flats are the epitome of preppy style. The uncomplicated shoe helps you float through the day with the poise of a ballerina and the unaffected air of an Ivy League trust-fund baby. But here are some ways of styling from the recent runways that's likely never occurred to them: chunky socks and leather hot pants, or with a tiny skort and a gingham puff-sleeve blouse. 

4. The Jewelry That Says I Belong to the Country Club 

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

5. The Skirt That’s Perfect for Breaking the Rules 

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

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

6. The Preppy Pants That Are Making a Comeback 

The prep revival isn’t just bringing chinos back; it’s reclaiming them. Leg shapes are getting wider (just like jeans), and pockets are getting deeper and more cargo-adjacent. Even thrown together with basic clothing like a plain white T-shirt, a directional belt, and one of the best loafers above, these casual-cool pants feel miles away from the school and pharmacy uniforms where they spent most of the 2000s—but they’re still functional. 

7. The Sweater That’s Gaining Popularity in Every Corner of Prep Culture 

Sweater vests are the versatile little layer that every corner of modern prep seems to embrace, from dark academia (with a button-down, Blackwatch tartan pleated skirt, and chunky loafers) to grandpa-meets-Gen-Z-chic (with a contrasting striped shirt and chinos) to sexy yet preppy (with low-rise denim and nothing underneath). They're connected to the hallowed outfits of prep's origins but are just as likely to be worn by present-day style icons like Bella Hadid and Harry Styles.

How to Recreate the Preppy Style

To achieve the perfect preppy look, focus on key pieces that embody the essence of the aesthetic. Most of these pieces are ones you already own in your current wardrobe. So, no need for any additional cost. You just need to mix and match these preppy staples. To channel your inner gossip girl, focus on five key elements: 

Preppy capsule wardrobe

A Preppy wardrobe is filled with classic staples that last forever. Incorporate formal, classic pieces with more fun pieces using your unique personal style to create endless preppy aesthetic outfits. A preppy wardrobe includes crisp button-down shirts, navy blazers, khaki pants, sweater vests, rugby shirts, polo shirts, boat shoes, and a Pleated skirt.

Incorporate Classic Patterns

Incorporate classic patterns such as plaids, stripes, and argyle prints to elevate any outfit effortlessly. From plaid mini skirts to oxford shirts, these patterns add a touch of preppy elegance.

Master the Art of Layering

A vital element of the preppy aesthetic is the layering of casual sports items with more traditional, formal pieces. A critical aspect of the preppy aesthetic is the layering of casual sports items with more traditional pieces. This combination, such as a rugby shirt paired with a tweed navy blue blazer and a tennis skirt, gives the preppy look its distinctive charm.

Choose the Right Colors for Your Aesthetic

The preppy style leans towards a neutral color palette, with a pop of color here and there. Experiment with colors, opting for traditional neutrals, pastel hues, and pops of bright colors to add personality to your outfit. Think grey, brown, beige, white, and red. These are a few of the colors dominating the preppy aesthetic color palette. 

Accessorize Your Outfits

To complete the look, remember to accessorize with ties, pearl earrings, and headbands. Pair your loafers with socks for the perfect preppy vibe. 

Old Preppy Style vs New Preppy

The essence of preppy fashion has remained consistent over time but has evolved to embrace contemporary trends and influences. Old preppy style resembled old money style and featured a more formal and structured aesthetic, emphasizing traditional pieces like tweed blazers and pleated skirts. However, the contemporary preppy style embraces a more relaxed and eclectic approach, blending classic elements with modern silhouettes and unexpected combinations. 

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33 Preppy Outfit Ideas for the Modern Woman

1. Get Your Monogrammed Gear

Your average pullover sweatshirt is transformed into a varsity look with one letter — collegiate font patches are the ultimate preppy accessory.

2. 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 2024.

3. Vintage 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.

4. 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.

5. 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.

6. Sweater (Vest) Weather

Layering a sweater vest over a preppy button-down is perfect for days when you want to get away with wearing leggings while still looking fashionable.

7. 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.

8. Plaid on Plaid

Don't be afraid to wear a monochrome look with prints. Hailey Bieber knows that plaid is neutral in classic shades like grey, black, or white.

9. Belts, Caps, and Bags

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

10. Gothic Peacoat

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

11. 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 with a vintage concert tee and pants.

12. 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.

13. Clean White Turtleneck

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

14. Updated Penny Loafers

Make your classic penny loafers feel fashiony with cropped jeans and cute striped socks — any outfit instantly becomes preppy when you add a pair of black slip-on loafers.

15. A Classic Varsity Sweater

Nothing says "preppy" like a classic Lacoste varsity knit. Wear your oversized with slim joggers, or dress it with a slim trouser and boots.

16. Suit and loafers

This outfit beautifully shows the striking similarities between the old-money style and the preppy aesthetic. The grey blazer and skirt set paired with a crisp white shirt exude the classic sophistication often associated with old money style. Yet, with the addition of white socks and chunky loafers, the outfit transforms into preppy fashion.

17. Mix and Match

Remember when we talked about patterns being one of the preppy fashion elements? so don’t be afraid to mix different patterns in your outfit. Just remember to mix different sizes of patterns together and choose colors that blend well together. Argyle pattern is essential in preppy fashion; it adds sophistication and heritage to any outfit.

18. Vest, mini skirt & a tie

Nothing screams preppy style like a tie! It’s easy to add a preppy touch to your classic outfits. Wear it with a blazer, knit vest, or mini skirt. Don’t forget to finish off the look with chunky loafers and socks.

19. layer up

This is the ultimate Ralph Lauren look a checked skirt paired with a sweater. Layering is an essential element of preppy fashion, so Don’t forget to layer a white shirt underneath for extra warmth and a preppy touch.

20. Pop of color

I’m sure you’ve seen the red tights trend on social media; this outfit is an excellent example of how you can incorporate this trend into your preppy aesthetic outfit.

21. Tennis skirt and sweatshirt

A tennis skirt is a staple for your preppy aesthetic wardrobe. Pair it with a collared sweatshirt, or layer a white shirt underneath. Finish the look with a white headband and some accessories.

22. Pleated skirt & trainers

How stunning is this outfit? The red bag adds the perfect touch of color, and the pearl necklace just adds a super chic element to the look. If you want to recreate this outfit in winter, it’s always a good idea to layer a turtleneck sweater underneath for extra warmth.

23. Monochromatic Cozy knits

Pleated skirts are a preppy wardrobe staple you can easily dress up or down. Pair them with a button-down shirt and layer a cable sweater on top. Bonus points if you choose similar colors for a monochromatic preppy outfit.

24. Stripes & a White shirt

This is a stunning outfit, Changing from loafers to ballerina flats. layer a striped sweater over a shirt dress or pair it with a pleated skirt and layer a white shirt underneath. Stripes are synonymous with the preppy style and add a chic touch to any outfit.

25. White shirt & Pleated skirt

This is such an easy look to recreate. you can wear it year after year, and it will never go out of style because it incorporates classic pieces. Pair a white shirt with a grey pleated skirt, and finally, add a pair of heeled loafers and socks to tie the look together and get the preppy vibe.

26. Jeans & Knit

After finishing this blog, I noted all 10 outfits included skirts so I thought I would give you a bonus outfit with pants. Although the preppy style focuses on skirts and dresses, you can nail the style with jeans, ballet flats, and a navy sweater layered over a shirt. The perfect casual preppy outfit.

27. jacket | t-shirt | jeans | shoes | watch

Lady jackets have my heart and are also within the preppy aesthetic category. From quickly dressing up a pair of jeans and a white tee to being the focus of an entire outfit, this piece is versatile in the best ways and truly perfect for styling year-round! More structured and polished than a knit cardigan, for example, lady jackets allow you to add structure and poise to the most basic looks, regardless of the season, and that’s exactly what we’re going for here! 

Many also consider this preppy look French-inspired, as it uses many elements I love about French fashion. Take a break from your skinny jeans and experiment with a different denim fit by starting this look with these 90s straight jeans. This straight silhouette is the right fit for a timeless and elegant pair of jeans—not too tight or loose! On top, an elbow-sleeve t-shirt does the trick, offering slightly more coverage to keep you comfortable and warm. 

Layer your navy lady jacket on top, instantly adding that preppy charm to your ensemble. Opt for a delicate gold watch as your main accessory, elevating your outfit with a more polished flair. As for shoes, these ballet flats will slip onto your feet quickly, complementing your look and level of comfort throughout the day. 

28. Linen Shorts + Polo Cardigan Sweater + Mary Jane Flats + Cat-Eye Sunglasses + Tote Bag

The preppy aesthetic can be confusing and lead to many misconceptions among those who aren’t super familiar with the style—one of the main ones being that there is no such thing as a casual preppy outfit. While this is not true, this outfit is here to disprove this theory officially and show you exactly how this simple look falls under the preppy aesthetic. 

More than specific types of outfits or clothing pieces, the preppy aesthetic is about using classic styles and silhouettes for elegant overall ensembles. While these looks can include many accessories, simplicity is also a way to find the perfect preppy look.

29. Pleated Linen Shorts + Button-Down Shirt + Leather Belt + Cashmere Sweater + Ballet Flats + Tote Bag

Bright colors can sometimes be fun to incorporate into looks, but neutrals have my heart! Also ideal for spring, this next outfit is a dream for anybody who loves classic neutral shades – and a pop of light blue. These pleated linen shorts kick off the look. Shorts can often feel too casual if you are not used to styling them within this aesthetic, but there are many ways around this obstacle when crafting genuinely classic looks during the warmer months of the year. Opting for fabrics like linen, for example, instantly adds a luxurious texture to your look, setting the Outfit's tone and balancing the shorts' more casual design.

On top, this blue button-down shirt continues to dress up the bottoms. Style your shirt by rolling up the sleeves and tucking it into your shorts for a better fit and overall look. Whether you wear your cashmere sweater tied draped over your shoulders, keep it inside your tote, or have it on, this piece can be integrated into this look with several different chic wayside-leg jeans + button-up shirt + ballet flat + leather tote + leather strap watch. 

30. Bringing Another Classic Tone 

This sweater adds a beautiful extra layer to the outfit's neutral color palette. For true lovers of the preppy aesthetic, this next look can undoubtedly be found in your closet! Starting with these slim, wide-leg jeans, this look again relies on classic wardrobe staples and mindful accessories for the natural preppy effect. On top of that, there is nothing wrong with this Oxford button-down shirt. 

When it comes to styling, there is no unflattering way to wear this piece: tuck it in or leave it out, roll up the sleeves, or leave it as is! This classic beige bag is a perfect accessory for this basic look, tying in with the two-toned ballet flats that tie the final aspects of the look together. Incorporate this black and gold watch into the look for an extra touch of black for an all-around elegant outfit you will keep coming back to over and over again. 

31. Try a Tie

Pairing a tie with a plaid skirt will add a bit of classic prep school energy to your next preppy fit. By choosing statement accessories, you can keep the look from skewing too academic. 

32. Try Prep Sweats

Who says preppy can't be comfy? The next time you feel like rocking sweats, add a blazer, a baseball cap, and a crewneck sweatshirt tied over your shoulders in classic prep fashion.

33. Opt for Argyle

The prep aesthetic has always brushed shoulders with activewear, but you don't have to wear a tennis skirt to get in on the trend. Instead, try a matching skirt set in a preppy print like Argyle. 

20 Preppy Outfit Ideas for Guys

1. Denim Prep: Modern Takes on Classic Blue

A denim jacket is your friend when it comes to preppy style. Forget club blazers and tweed; a jean jacket adds a more casual flair to tailored trousers and loafers, especially when combined with a striped polo and logoed baseball cap.

2. Winter Prep: Stay Warm in Style

Take inspiration from those 90s Ralph Lauren ski jackets and opt for a color-blocked version, which works as a statement piece and a way to protect you from the cold. Combine it with tailored corduroy trousers and a beanie, and you’ll be the coolest guy in the room, whether in a ski chalet or not.

3. Mix It Up: Preppy Pieces with a Twist 

With a tweed or club blazer, this look would be the definition of classic prep. But swap out the tailoring for a fleece jacket, and it’s instantly injected with a more contemporary feel, which perfectly complements the worn-in jeans and baseball cap.

4. Varsity Jacket: Channel Your Inner Jock 

Varsity jackets have a long lineage in the world of prep. The good news is that you don’t have to be a college baseball team sophomore to wear one. Look for simple designs in muted colors like bottle green and combine them with tailored trousers, roll necks, and suede boots. 

5. Monochrome Prep: Less is More

Preppy style might traditionally be all about color—from loud madras shirts to vibrant polos and punchy tweed—but for a contemporary update, try a muted monochrome look consisting of a plain grey varsity jacket, black shorts, a white tee, and penny loafers.

6. High/Low Dressing: Mix and Match for a Fresh Look

A crucial part of prep 2.0 is high/low dressing. That means combining something high-brow, such as tailored trousers, with something more casual, like a streetwear hoodie. This look shows why this combo is an easy route into the preppy game.

7. Classic Ivy League: Stick to the Classics 

If you are a stickler for tradition, there’s no harm in keeping things old school. Go for a classic American-tailored look with a sharp double-breasted boating blazer, Oxford shirt, chinos, and loafers, and you can’t go wrong.

8. Summer Prep: Think Details for Warm Weather Looks 

While not a classic look on paper, it’s all about the details. The minor things can infuse a bit of prep into an outfit, like the subtle silk, cravat-like neckerchief tied underneath the Cuban collar shirt here, once the preserve of Ivy League professors and now a summertime flex.

9. Preppy Summer Staples: Go for the Basics 

For a simple spring or summer look, this outfit uses classic prep staples – a striped linen shirt, pleated shorts, and canvas belt – and renders them in a warm-weather context. Finish with cream espadrilles and tortoiseshell shades for an Italian-inspired twist.

10. Relaxed Preppy Tailoring: Keep It Easy 

Regarding preppy tailoring, it’s best not to try too hard. It can be all too easy to fall into Carlton Banks' territory, not in a good way. To stay on the right side of stylish, stick to classic shades of navy and off-white and pay attention to the fit. Consider more relaxed cuts than you’re perhaps used to, combining wide-leg trousers with a boxy, unstructured blazer, as shown here.

11. The Rugby Shirt: A Prep Classic 

The rugby shirt is the UK incarnation of the varsity jacket or the letterman sweater. It’s a public school classic, and the upper class has appropriated it for weekend wear for decades. But do it well, and it’s so much more than that. Look for one with a boxy fit and a simple striped pattern, and wear it with everything from selvage denim and sneakers to khaki pants and loafers.

12. The Madras Shirt: Add a Splash of Color 

While it’s undoubtedly risky business, the Madras shirt is a style classic. Typically cut from jazzy fabrics featuring loud check patterns, the style is perfect for a splash of summer color. Try it yourself by keeping the rest of the outfit muted and anchoring your top half with neutral-tailored trousers and leather boots.

13. Preppy Color Palette: Brighten Up with Neutrals 

The preppy aesthetic has long been defined by bright, bold shades – from scarlet red to burnt orange – whether via polo shirts or the fibers in its tweed jackets. Try it yourself by injecting a splash of color into your top half with a statement hoodie. Keep everything else simple and finish with canvas high-tops for some old-school flair.

14. Mod Prep: Borrow from the Best 

The best bits of mod style were borrowed from prep, from the penny loafers to the jackets and sharp tailored trousers. Combine the lot, throw in a knitted polo for good measure, and you can get your bit of 60s Carnaby Street action, whether you’ve got a Vespa or not.

15. Consider Texture: Add Depth to Your Look 

Here’s a contemporary take on prep that’s perfect for 2024. It works largely because of the color palette of browns and naturals and the texture. The sweatshirt's cotton jersey (a prep staple) complements the jacket's corduroy, while the bi-weave trousers work perfectly with the suede loafers.

16. Sportswear Inspired: Use Your Old Gym Clothes 

Prep has heavy roots in the sporting world, from its letterman jumpers to varsity jackets. And while sweatpants don’t scream Ivy League, they add a youthful feel to a rugby shirt and sneaker combo, making it ideal for a relaxed weekend look.

17. Moneyed Smart Casual: What to Wear for the Yacht Club 

There’s something about a polo shirt tucked into a pair of stone trousers that screams ‘Gatsby on his day off.’ While the jumper tied around the shoulder may take it too far, this is a timeless prep look ideal for many a summer sporting event.

18. Relaxed Tailoring: Dress for Success (Without the Stress) 

The sports coat was a core part of the original prep aesthetic, and it’s a garment that translates well to today’s world with the continued casualization of dress codes. An unstructured, knitted blazer such as this can be thrown over everything in your wardrobe – from jeans to chinos – helping you instantly smarten up without looking stuffy. Combine it with textured wool trousers and a knitted polo shirt, and you will have an outfit that works just as well for business casual lunches as dinner and drinks with your partner. 

19. The Preppy Shirt Tuck: Just Tuck It In for a Smarter Look 

Sometimes, it just takes a shirt tuck to look at the preppy treatment. So, next time you wear a button-down shirt, try tucking it into mid-wash jeans, and you’ll instantly feel smarter and more refined. 

20. Old Meets New: The Best of Both Worlds 

This is a definitive prep look that references old and new. It incorporates almost every garment associated with the Ivy League; it sees a Madras shirt tucked into mid-wash jeans, with a varsity jacket and camel overcoat layered over the top. Not only that, it’s then finished with loafers and a tonal baseball cap. Half street, half classic, it showcases everything great about prep style in 2024.

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British Preppy Style for Men

Shaping the British Preppy Style

The preppy aesthetic has gone through many iterations since its inception. The origins of British prep style can be traced back to the casual clothing of Ivy League schools and their athletic teams. The look was quickly adopted by the upper crust and popularized in the media. Today, the preppy style is back big, with distinct British and American variations. 

The go-to pieces of the British style differ slightly from the American version. For instance, whereas the American preppy style calls for bright colors and bold prints, the British prep style favors more muted tones and classic patterns like houndstooth, herringbone, and plaid. 80s American sitcoms popularized the look; now it’s back and more fabulous than ever. Think less country club and more modern-day eccentric professor.

The Hallmarks of British Preppy Fashion

The casual apparel of students from Oxford and Cambridge universities inspired modern British preppy fashion. British preppy style for men effortlessly combines professorial pieces with sports attire. This ingenious mixing and matching revolutionized how men dress over the last century. It also laid the foundation for prep styles and various types of business attire. Go-tos include Barbour jackets, blazers, rugby shirts, chinos, and repp ties. Worsted wool, tweeds, and plaids reign supreme. 

Mixing Sports and Tweed for Men’s Preppy Style

Men’s preppy style incorporates the athletic wear of Britain’s most treasured pastimes. Rowing and horseracing are two prime sports that influence this aesthetic. From the Henley Royal Regatta to Royal Ascot, the bright colors, striped patterns, and single-breasted blazers are preppy staples. Pop on a grey flannel herringbone jacket over a color-block rugby shirt to take this style for a spin. Round out your ensemble with midnight blue slacks and boat shoes. You can roam from the spectator stands to drinks with friends in a jiff.

An 80s Throwback: Preppy Style for Men

The prep movement gained a strong foothold in men’s fashion over the 20th century. American prepsters, including President John F. Kennedy and Hollywood legend Paul Newman, were popping up. Likewise, styles were spotted on campus, in the office, at the stadium, and everywhere. Enter 80s preppy style. This era of men’s fashion, known for its bold designs, accelerated the boundaries. With sportswear designers like Ralph Lauren emerging, affordable luxury in brightly colored polos and crew-neck sweaters became accessible to everyone. 

Southern Preppy Style for Men

Let’s head south to Palm Beach. Southern preppy style starts in this well-heeled Florida city by the sea. The coastal elements found in the preppy style for men are correct at home here. This southern sensibility boasts pastel colors and lightweight materials. Madras and seersucker are critical fabrications that offer tons of polish and sophistication while keeping you cool. These lightweight cotton are breathable, making them ideal for warm-weather wardrobes. Traditional plaids and stripes reinvented for summer? Sign us up! 

WhatColors’ Your AI Personal Color Analysis

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How To Dress Preppy On Any Budget

1. Invest in Quality Preppy Staples for a Timeless Look 

You'll want to invest in quality preppy staples to build your wardrobe. The preppy aesthetic is all about timeless fashion; these items will never go out of style. Button-downs, polos, chinos, and blazers are foundational to the look. You can mix and match these items for various outfits that will last for years. 

2. Button Down Shirts 

No one does preppy better than Brooks Brothers, and one look at their selection of button-down shirts will explain why. These shirts have been a staple of Ivy League style for decades. They come in various colors, patterns, and fabrics to suit any occasion. You can wear them with shorts or chinos, underneath a sweater or blazer, or on their own to achieve a credible preppy look. 

3. Polos 

Polos aren’t the exclusive property of preppy style, but they’re not far off. A decent polo is a gatekeeper to a definable ‘smart casual.’ It’s infinitely more stylish than a tee but with fewer formal associations than a collared shirt. Therefore, it’s become an enduring feature of Ivy League adherents, who appreciate its stylish wearability. Ralph Lauren leads the way with polos; some think there’s nowhere else to look. 

4. Chinos 

There is a slight disdain for formality among adherents to preppy style, and replacing suit pants with chinos manifests this quiet disregard for being overdressed. Khaki chinos with navy is an enduring, reliable preppy ensemble. Bolder choices like salmon pink aren’t uncommon for preps with a braver constitution. 

5. Blazers 

A navy sports coat with gold buttons is about as prep as a photo of JFK on a yacht. Such an item can underpin a respectable wardrobe as it can be worn with anything: part of a full suit, shorts, or odd trousers. Your imagination defines the only limit. 

6. Pullovers 

Crew-neck pullovers and knits are an immediate go-to for the casual end of the preppy spectrum, but that’s not to say you can only wear them outside the corporate stratosphere. Cable knits look smart with chinos on nippy autumn days or under a suit jacket for dapper insulation during colder months. 

7. A Word On Preppy Accessories 

Regarding accessories, there’s an undeniable appeal to the preppy repp tie. If a preppy dude wears a tie, this is his first, and often last, choice. Originally part of collegiate uniforms, the distinctive striped tie is something most preppy aspirants add to a white button-down and blazer look.  Preppy knitted ties are a common alternative. 

They’re suitable for when a tie is required for a formalizing touch or splash of color but when a conventional silk tie is a bit too much—worn with a cable-knit button down, forgetting the blazer, for a dashing outfit that doesn’t disservice to the ‘smart casual’ ticket. Bowties are an irreverent alternative to traditional neckties that add a touch of Ivy-style charm to any outfit.  They’re probably more popular with a professor than a student, but they're still part of the style. Invest at your own risk. 

8. Don't Try Too Hard When Going For Preppy Style 

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

9. Never Go Full Preppy Style 

This ties in with caveat numero uno. Prep style is all about being effortless. There’s no need to incorporate everything at once. If you spend most of your time in Bintang singlets and trackies, your mates might ask what the story is if you rock up to knock-offs in boat shoes and a button-down with a sweater around your shoulders. It takes a brave bloke to cop that roasting, so don’t go full retard. Stick to one or two pieces to start. Avoid imitating your American lacrosse mates head-to-toe, even if they look the business and score more chicks than you do.

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25 Preppy Clothing Brands You'll Be Shopping From All the Time 

If you love the preppy aesthetic, investing in classic pieces that will last a lifetime is probably time. The first step? Familiarize yourself with the top brands that define the style. We’re talking about Ralph Lauren, J.Crew, and Brooks Brothers—labels perfecting their preppy styles for decades. 

Below, we’ve rounded up 25 preppy clothing brands that deserve a spot in your closet. Whatever you want to complete the *chef’s kiss* coastal grandma/quiet luxury look you’re trying to achieve, there’s something here for you. From chic sweaters to gorgeous dresses and elevated workout clothing (who doesn’t love a tennis outfit?!), you’re about to be transformed into the Hamptons girl of your dreams!  

1. Nautica Solid Polo Dress  

Nautica’s identity as a coastal preppy brand has been consistent since the brand’s inception in the ’80s. The brand features many preppy styles, such as striped blazers, shirts with sailboat graphics, and even classic polo dresses like this one.   

2. Recreational Habits Black Tee  

Recreational Habits hopes to make preppy clothing accessible to everyone. They have fun activewear pieces like this tank (and matching skirt!), sweet sweaters, and dresses.   

3. Ralph Lauren Flag Cotton Crewneck Sweater  

Ralph Lauren is an OG. The brand has been around since the ’60s and has become a staple for classic preppy pieces like polo shirts, blazers, and an American flag sweater. Picture yourself on a beach this summer with this layer over your shoulders. Très chic!  

4. J.Crew Boatneck Muscle T-shirt in Stripe Mariner Cotton  

I’ve always considered J.Crew a 10/10 go-to brand. They have solid basic tees, jeans, sweaters, jewelry...you name it. Not only that, but J.Crew is also a great place to shop for preppy pieces. This boatneck muscle tee with blue and white stripes radiates a mature, elevated, preppy girl look.

5. L.L.Bean Women's Bean's Classic Ragg Wool Sweater, Crewneck Fair Isle  

If you want to nail the preppy look this fall and winter, I’d highly recommend looking at pieces from LL Bean! The retailer has an outdoorsy vibe, perfect for those who like to spend time in nature in the year's colder months. Pair this Fair Isle sweater with your favorite jeans for a casual get-up.  

6. Jack Rogers Lauren Mid Heel  

You gotta have some on-theme shoes to match the whole moment! Enter: These Jack Rogers heels. The iconic round medallion detailing is essential to Jack Rogers’ shoes and is an instantly recognizable feature in preppy fashion.   

7. Barbour Kelley Quilted Vest  

JSYK Barbour is a widely known brand that even the English Royals wear! They make great outwear that is fundamental to a year-round preppy wardrobe. Consider this quilted vest a transitional piece to prep-ify your ‘fit.  

8. Brooks Brothers Relaxed Linen Tennis Sweater  

You may see the brand Brooks Brothers and think of men’s suits. However, Brooks Brothers has some great preppy pieces for women, like this gorgeous v-neck sweater with the classic white stripes around the neck and sleeve endings.  

9. Lands' End Women's Linen Sleeveless Midi Dress  

Lands’ End began as a company that sold sailboat equipment and then transitioned to apparel in the late 1970s. This nautical influence has taken over the style of the brand’s clothing, including this lightweight linen dress, which is the perfect piece for a stroll in a coastal beach town.  

10. Vineyard Vines Silky Slip Skirt  

Credit: KATE LACEY. Vineyard Vines might be the first brand that comes to mind when considering preppy style. They’ve seriously solidified their spot in this specific fashion market! This gorgeous slip skirt paired with a belted cardigan will still give you a preppy look while making you look chic.  

11. Old Navy Oversized Button-Down Boyfriend Shirt  

Look, I understand that preppy clothes can sometimes have steep price tags. However, many inexpensive brands feature pieces you can style preppy, such as this button-down from Old Navy! Pair it with white jeans and a thick headband for a classic preppy look.  

12. Southern Tide Staci Active Ruffle Tank  

Preppy clothing isn’t limited to fancy dresses or sweaters. Southern Tide makes great preppy activewear, such as this tank with ruffled straps and this printed tennis skirt. This whole fit is perfect for playing pickleball with your family!  

13. Lilly Pulitzer Shelli Stretch Top & Sarissa Stretch Short Set  

Lilly Pulitzer has been one of my favorite preppy brands since I was young. They carry the most quintessential preppy pieces—from seashell-printed maxi dresses to short sets like the one shown here; Lilly pieces will 100 percent give you the ~look~ you’re going for.  

14. English Factory Contrast Scalloped Trim Cotton Midi Dress  

English Factory offers several elevated basics and preppy pieces, like this dress. It features a scalloped hemline, which is very common in preppy clothing!  

15. Ann Taylor The Short Patch Pocket Jacket in Confetti Fringe Tweed  

Ann Taylor carries plenty of polished and sophisticated styles that can also give you a preppy look. How fab is the tweed and gold-button combo on this jacket?  

16. Tommy Hilfiger Gingham Pull-On Seersucker Short  

Tommy Hilfiger is another classic brand in this fashion realm. The brand started in the ’80s and features preppy staples like polo shirts, dresses, and blazers. This gingham blazer and shorts set can be worn together or separately to make you look preppy any day.  

17. Sperry Authentic Original™ Boat Shoe  

You must have a boat shoe to lean into the trend. I don’t make the rules! But more specifically, Sperry Top-Siders. Sperry shoes were developed as boating shoes in the early 20th century and have become one of the most well-known symbols of preppy fashion.   

18. Tuckernuck Milana Shorts  

Tuckernuck is a retailer that carries many brands and produces clothing under its eponymous label. The brand name comes from the tiny island off the coast of Cape Cod, a town known for its preppy fashion. So get yourself some Tuckernuck pieces, like these classic white shorts, perfect for a summer on a boat in the Cape. I can see the Instagram pictures already! 

 

19. Eloquii Yarn Dye Striped Straight Leg Pant  

Like a few brands on our list, Eloquii doesn’t outwardly present itself as a preppy brand. However, they have several pieces that radiate that vibe. Check out these striped straight-leg pants that could enhance your preppy style, especially paired with the matching top!  

20. Posse Harvey Skirt  

During her wedding weekend last year, Sofia Richie Grainge wore a two-piece set from the elegant and classic brand Posse. This brand is the definition of sophisticated and subtle preppy vibes, IMO. Style this sleek white maxi skirt with a striped shirt for the ultimate quiet luxury look.  

21. Lacoste Women's Ultra-Dry Anti-UV Golf Polo  

Lacoste is a French brand founded in the early 20th century by a tennis player. And let’s BFFR, tennis, and preppy go hand-in-hand, so you best believe Lacoste has all the preppy fashion. This sleeveless polo is perfect for just throwing on while still looking put-together.  

22. Reformation Tossa One Piece Swimsuit  

Keep your preppy style at the beach by wearing this stunning one-piece from Reformation. You’re just missing a floppy hat and bold jewelry!   

23. Universal Standard Bardot Wide Sleeve Cotton Sweater  

Universal Standard may not be marketed as an outwardly preppy brand, but it features a slew of pieces that match the aesthetic perfectly. I love this simple, striped, wide-sleeve sweater you can easily dress up or down.  

24. RE ONA Bobbi Shorts  

Don’t sleep on RE ONA when it comes to preppy fashion! The brand has many incredible classic pieces, like these mid-length shorts that’ll become a regular in your rotation.  

25. Longchamp Le Panier Pliage S Basket bag  

Round out your outfit by treating yourself to a classic preppy bag: the Le Panier Pliage from Longchamp. It’ll hold all your essentials (phone, keys, and wallet) and be the perfect finishing touch for any outfit.

Try AI Personal Color Analysis For Free Today

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

Based on your skin, eye, and hair color, find the perfect nail colors with our WhatColors Nail Color Generator. Get your color analysis done within 60 seconds with WhatColors’ AI Personal Color Analysis app. Download our app for free today on the App Store or Google Play store.