There’s something inherently appealing about preppy style. It’s timeless and polished yet still manages to feel fresh and modern. Of course, the charm of the preppy aesthetic doesn’t matter if you can’t pull off the look. Imagine showing up to a gathering and feeling completely out of place in your outfit. Sure, your clothes might be nice, but they aren’t you. Instead of blending in with the crowd, you feel like an outsider, as if you were walking in from a different era. If you’ve ever worried about looking outdated in your outfits, this guide on how to be preppy can help. With its focus on blending traditional elements with contemporary styles, you’ll learn to achieve a classic preppy look that’s all your own.

WhatColors’ AI personal color analysis app can help you achieve your goals for a polished preppy style even faster. The app provides tailored insights about your unique color palette to help you choose the shades that complement your natural features and personal style.

Table of Contents

• What is the Preppy Style?

• 12 Preppy Men's Clothing Essentials

• 13 Classic Basics Every Preppy Girl Needs

• 4-Easy Guide on How to Be Preppy

• How to Be Preppy After 30 Without Looking Ridiculous

• How to Be a Preppy Man in the Menswear Age of Chaos

• The Key to Dress Unpretentiously Preppy

• 43 Must-Know Preppy Clothing Brands

• Try AI Personal Color Analysis For Free Today

What is the Preppy Style?

The preppy style is a fashion subculture with roots in Ivy League collegiate aesthetics. Traditionally, prep, preppy, prepster, or any other variation were used to describe a subculture of upper-class youth born into old money in the Northeastern United States. 

They would attend their family’s alma mater, typically one of the eight schools classified as Ivy League:

• Brown University

• Columbia University

• Cornell University

• Dartmouth College

• Harvard University

• Princeton University

• The University of Pennsylvania

• Yale University

As these prestigious halls of education are otherwise known as preparatory schools, you can see how the moniker of prep and preppy style came to be. Today, the term preppy is far looser and is regularly used in high schools across North America and parts of Europe. It still accurately describes the subculture of those who have adopted a manner of:

• Speech,

• Vocabulary

• Dress

• Manners

• Etiquette

Where Did Preppy Style Come From?

The preppy style emerged in the 1900s when the children of wealthy families began to attend preparatory schools. These schools were designed to prepare students for Ivy League colleges. The look was rooted in the athletic uniforms the teams wore at these elite institutions. 

In time, styles seen on campus began infiltrating popular culture, and the upper class adopted the more formal versions of these looks as everyday attire. By the 1940s, preppy was used to describe the narrow, stereotypical version of what we now consider the Ivy League style.

Historical Origins

The association of the look with old money and privilege was solidified in the 1950s with the publication of The Secreta of the New England Upper Class in Life Magazine. The magazine featured a pictorial on the lives of the children of the elite who attended Ivy League schools. The article focused on their exclusive social clubs, and the accompanying images showcased their distinct style. 

In the 1960s, Ralph Lauren popularized the preppy look, using it as inspiration for his early collections and marketing it to the masses. The trend has ebbed and flowed in popularity since then but has remained a staple in American fashion.

What Does Preppy Style Look Like?

Clean lines, classic cuts, and a polished, timeless look characterize the preppy style. Key items include:

• Polo shirts

• Chinos

• Cable knit sweaters

• Boat shoes

While many of these staples are practical for time spent on the water or the golf course, they can be mixed and matched for various occasions, both casual and formal.

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12 Preppy Men's Clothing Essentials

1. Preppy Style Jackets and Blazers

The navy blazer stands as the quintessential preppy style jacket. You can wear it with various outfits, providing a polished touch to even the most casual ensembles. The classic version is a navy blue, single-breasted jacket with notched lapels and three brass buttons. 

You’ll often find them with an embroidered logo that’s nautical. The double-breasted look also works well, especially for that extra nautical feel. Of course, many companies make these blazers, but the most popular today seem to be from Ralph Lauren and Brooks Brothers.

2. Preppy Style Shirts

Oxford Button Down Shirts

Button-down collars were initially introduced by Brooks Brothers in 1896 and have remained popular as a way of dressing down a regular dress shirt. Using buttons that fasten down the collar points on the front of the shirt meant these were almost exclusively worn as sport shirts until the mid-1950s. 

Still considered a sports shirt in most circles or as a way to give casual flair to elegant attire, these shirts are trendy in prep culture and are often paired with the iconic navy blazer and a repp tie.

Polo Shirts

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

• Silk

• Merino wool

• Various synthetic materials

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

3. Preppy Style Trousers and Pants

Chinos

Chinos are trousers made from a twill fabric, originally 100% cotton. While they can be found in synthetic blends now, the best are still made of cotton. Brooks Brothers offers a superior selection, as do many other fine clothes. 

Today, they come in many colors, but the most common is khaki, which is still very popular in coastal culture.

GTH (Go To Hell) Pants

GTH pants take some serious getting used to. This style will surely net you either looks of disdain or nods of approval as you walk around in them. They are bright pants with sometimes bold embroideries on them of:

• Sailboats

• Anchors

• Lobsters

• Crabs

• Frogs

• Variety of other icons

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

Nantucket Reds

Nantucket Reds are an essential component of prep culture. The red pants, shorts, shirts, hats, and other articles were initially distributed by Murray’s Toggery Shop in Nantucket and are guaranteed to fade to an almost rosy pink. 

They are traditionally pants, but today, they consist of an entire selection of clothing and accessories that are incredibly popular to the point of being legendary in:

• Martha’s Vineyard

• Cape Cod

• Their birthplace of Nantucket

4. Preppy Style Knitwear

Argyle Sweaters

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

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

Cable Knit Sweaters

Cable knit sweaters are classic and will never go out of style. No matter whether they are made of:

• Cotton

• Wool

• Cashmere, with sleeves or without, they are a staple of a preppy wardrobe.

A crew neck is the way to go if you wear bow ties, while ties look great with V-neck sweaters. For a soft, casual outfit, look for a melange two-tone yarn, which lends the sweater a mottled, gentle look.

Rugby Shirts

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

Tennis & Cricket Sweaters

Tennis or Cricket sweaters are a must-have in a preppy wardrobe. Take a look at our dedicated Tennis sweater article here.

5. Preppy Style Footwear

Boat Shoes

Like many staples in prep style, you either love or hate boat shoes. While many credit Sperry Topsider with the initial introduction, and most people consider them the quintessential boat shoe, many companies today make them. Boat shoes are pretty much exactly what they sound like. 

They were created as non-slip shoes for sailing. They are generally made of leather but can be crafted from other materials, such as canvas. They are typically worn without socks as casual shoes and are tied using leather boat shoelaces.

Loafers

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

Loafers are a casual shoe, but recently, many preps have begun wearing them with lounge suits or to work at offices with a more relaxed dress code. They come in various styles, colors, and materials and occasionally feature tassels or decorations on the front of the shoe. For a detailed discussion of loafers in all their varieties, read the Ultimate Loafer. 

Guide.

L.L. Bean Boots

Founded in 1912 by Leon Leonwood Bean, they quickly became known for their boots. Initially, they were hunting boots made of rubber and organically treated full-grain cowhide to resist water. A crepe rubber sole and contrasting brown or tan uppers achieved the characteristic look. While most boots today are lined with Gore-Tex, a simple wool lining was the norm back then. 

Many would give an arm and a leg to find new old stock boots in their size, but even the current version of Bean boots is so popular that the company's annual sales are north of 1.5 billion. Of course, they now sell all kinds of other outdoor-related items, but Bean boots in different heights and variations are still a favorite with preps.

White Shoes

White buckskin shoes, also known as white bucks, are a popular preppy companion to seersucker pants, cocktail parties, horse races, or anything related to summer. Paired with linen, chinos, or seersucker, they give the wearer a debonair, seasonally appropriate look.

Buckskin Leather

Buckskin leather is technically from male deer, but today, cowhide is often used instead because it is less expensive and more widely available. In the U.S., most buckskin shoes show the backside of the leather, which has a texture similar to suede, but the front side of buckskin leather can be very nice as well. 

Many white bucks have lightweight, red rubber soles, although they can also be found in Goodyear construction with classic leather soles.

6. Preppy Style Outerwear

Barbour Wax Jacket

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

Quilted Jackets

Like wax jackets, quilted jackets are a popular staple in a prep’s outerwear collection. To learn more about them, read our Quilted Jacket Guide.

7. Preppy Style Accessories

Anchor Bracelets

Anchor bracelets are exactly what they sound like: bracelets made from various fabrics and materials, usually rope, leather, or sailcloth, fastened with a small metal or plastic anchor that operates similarly to a hook. 

This jewelry is trendy in prep culture, both with men and women, and is about as nautical as it gets. While you can find these patterns in solid blacks and grays, the bright colors that are most popular are blues, greens, and pinks.

Belts

Colorful belts with motifs and stripes are integral to a preppy wardrobe. Often combined with brown leather and a brass buckle, these more or less flexible cloth belts are combined with chinos, Madras, or seersucker pants to create a bold look.

D-ring or Ribbon Belts

Traditionally called a ribbon belt, D-ring belts have been around since the mid-1960s, when J.Press introduced them. They provide a casual and fun flair to a typically conservative look. Some say that to wear them, you either need a sense of humor or a small budget since many D-ring belts are reversible, offering two-in-one belts. 

There’s nothing exclusive or luxurious about ribbon belts. They’re just a lot of fun with various patterns. From the iconic tri-stripe belts and the five-stripe versions from Ralph Lauren to ones with embroidered lobsters and sail-boats lining them, the belts, although traditionally made of polyester, rayon, and nylon, now come in a variety of fabrics and materials from sailing cloth to fine cordovan leathers.

Ties & Bowties

Although not exclusive to prep style, you’ll see more repp stripe neckties and bow ties as part of this aesthetic. Bold striped neckwear, resembling the collegiate stripes and crests, is a must here. Still, you can also focus on more professorial selections, including warm colors and small patterns, for a quieter take on preppy neckwear.

8. Madras

Madras is also a cotton fabric that is generally very lightweight and features a textured plaid design. In addition to pants, you can also find many pairs of shorts and jackets made of it. The Madras pattern is available in regular cotton and seersucker as well as patchwork madras, consisting of several pieces of Madras cloth being sewn together. This is very popular in the prep culture and is widely used by Brooks Brothers, among other fine haberdashers that focus on prep style.

9. Seersucker

Seersucker is another iconic fabric used in prep style. As a thin, cotton fabric that’s usually striped or checkered, it’s predominantly used to make summer clothing such as:

• Suits

• Shorts

• Pants

• Other men’s and women’s clothing

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

Wrinkled Texture

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

10. Sporting Leisurewear

This particular area is quite vast. From cricket sweaters and vests to rugby shirts and shorts, virtually any item of clothing you see being worn at a predominantly preppy sport can be considered an integral part of:

• Prep culture

• Fashion

Think of classic leisurewear from activities such as:

• Golf

• Tennis

• Cricket

• Rugby

• Sailing

• Equestrian apparel

11. Tweed

A proper prep can only be seen with any form of tweed during fall and winter. Indeed, a surefire way to revitalize a preppy outfit in cooler months, tweed in any capacity is a welcome addition to a prep’s wardrobe. Instead of giving you tweed advice here, head to our ultimate tweed guide and enjoy.

12. Timepieces

A classic, understated wristwatch is a must-have accessory for any Old Money Preppy dresser.

Look for a simple, elegant design from high-end designer brands like:

• Rolex

• Omega

• Cartier

Iconic Brands

• Rolex

• Omega

• Cartier

Style Icons

• Paul Newman

• Steve McQueen

• Grace Kelly

13 Classic Basics Every Preppy Girl Needs

1. A White Oxford (Button Down)

No preppy wardrobe is complete without a classic white button-down shirt. This piece can be used for years and spans all seasons. Adding a collared shirt under a sweater will polish your look much more. 

There is something sophisticated about a crisp button-down, so every prepster needs this staple piece.

2. Black Pants

Black pants are so classic- look to celebrities such as Audrey Hepburn or Grace Kelly. Not only do these slim your figure, but they go with everything. I prefer the Pixie Pants from J.Crew, but a pair from Old Navy or elsewhere will do great!

3. A Neutral Bag/Tote

Yes, we all love those super cute and colorful Kate Spade purses (I have one in bright hot pink!). You need a purse that can go with just about every outfit. I like this tote from Barrington Bags. 

It’s great for carrying laptops, books, etc. It’s also a great backpack alternative for college students wanting to look a bit dressier for class. I chose a gingham print for my bag (these are customizable) because I wanted to showcase my love for the print. I also think gingham looks excellent with many classic outfits.

4. Pearl Earrings

If you tell me you are a preppy dresser and don’t have pearl earrings, I don’t think I could believe the former. Pearls are essential for a preppy style. They are the epitome of class and sophistication; a preppy outfit is incomplete without them. 

Don’t spend tons of money on pearl earrings if you don’t want to! My pearl earrings are $3 from a local boutique. People usually can’t tell the difference!

5. Complimentary Watches and Bracelets

Every girl needs some arm candy to round out their outfit. You can add a class level to your outfit if you have several staple pieces that match, such as a bangle and a watch in one metal tone (such as gold).

6. Cap-Toe Flats

First of all, ballet flats are a must for a preppy wardrobe. Find an essential pair, such as black or nude flats, then add cap-toe flats. 

These are very Blair Waldorf but also very classic and Parisian. The cap-toe truly polishes the outfit by adding a flair of flirtiness and girliness.

7. Flouncy Mini Skirts

This first preppy trend is probably the biggest one I’ve seen thus far: flouncy mini skirts. This trend is the perfect cross between:

• Beachy

• Classy

• Flattering

My favorite way to wear a flouncy mini skirt is with a fitted solid-colored tank top or a tight body suit. This way, the skirt's volume can stand out without you looking like a cupcake. Whether you want to spend $300 or $30 on a flouncy mini skirt, I’ve got you covered.

8. Flouncy Mini Dresses

As you can see, flounciness is super hot right now. I love flouncy mini dresses because they’re super youthful. They can also be dressed up with block heels for a more fancy occasion and with some sneakers for a casual daytime look.

9. Matching Pajamas

I don’t know about you, but I feel put-together and sophisticated when wearing matching pajamas instead of the usual oversized tee and old pants. Matching pajamas have become a super popular preppy trend that I love. 

Roller Rabbit matching pajama sets are very popular and have been adopted by preppy fashionistas  (especially this one I own and am obsessed with).

10. Colorful Athleisure

Colorful athleisure (athletic leisure) is the ultimate comfy look for the preppy girl. Whether sweatpants, leggings, or comfy shorts, there’s always some form of color and/or pattern to make the look extra preppy and cute.

11. Puff Sleeves

Puff sleeves are so cute and have become a closet staple for preppy girls. I used to think puff sleeves were too mature and made me look like a mom, but I’ve realized this is false if you find the right pieces and can style them youthfully. 

A charming and preppy way to style puff sleeves is to wear a puff-sleeve mini dress, platform sneakers, and colorful sunglasses. I also love wearing puff-sleeve tops with jeans, especially in colder weather.

12. Colorful Swimwear

I initially hesitated to include this trend in this blog post because although it is preppy, it is also a universal trend. 

I’m adding it because I’ve never met a preppy girl wearing a plain black or white swimsuit! Color is a preppy girl’s best friend, so colorful swimsuits are a preppy staple.

13. Mary Janes and Loafers

When it comes to preppy kicks, nothing says school girl quite like classic loafers and Mary Jane shoes. Whether you prefer the shoe styles as flats, with heels, or with high platforms, stepping into Mary Janes or Loafers will have you giving every preppy school girl a run for their money. Just don’t forget to wear socks, especially knee-high versions, for the full preppy effect.

4-Easy Guide on How to Be Preppy

When you want to embrace the preppy aesthetic, it helps to break the process down into simple steps. Here are four straightforward ways to achieve the preppy look without overcomplicating it.

1. Incorporate Preppy Classics

Every fashion aesthetic consists of classic elements that embody the essence of that style. For example, signature pieces of the ballerina core include:

• White and pink pastel color schemes

• Flowy and frilled skirts

• Strappy shoes

You also embody that style whenever you wear specific clothing pairings and outfit options that are identifiable features of a particular aesthetic. Channel your preppiness with signature pieces to the aesthetic, like:

• Blazers

• Button-downs

• Vests

• Pleated skirts

2. Create Outfit Layers

Layers are also a quintessential style feature of preppy outfits. Traditionally, the various layers were a means of proper etiquette, ensuring that students and professionals dress modestly. 

They are a key feature of this American subculture and a great way to create chic winter outfits. Pair button-downs with sweaters, add vests and blazers as a top layer and wear stockings or knee-high socks to style a layered, preppy look.

3. Stick To Simple Shapes and Clean Cuts

Preppy outfits feature clean, well-kept, and professional appearances, alluding to its preparatory and posh cultural background. 

The smarter you dress, the more affluent you look. Stick to clothing with simple shapes and clean cuts to achieve a well-maintained, upper-class look associated with preppy culture.

4. Accessorize With Minimalistic Delicacy

Along with clean cuts and simple shapes, minimal accessorization also creates:

• Clean

• Put-together

• Smartly dressed appearances

Minimalist Accessories

It reduces the visual clutter to your outfit, keeping it simple, sleek, and chic. If you want to embellish a preppy outfit, opt for dainty accessories like:

• Plain headbands

• Pearl earrings

• Studs

• Hoops

• Bows

• Necklaces

Color Analysis by WhatColors

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 color with our WhatColors nail color generator. 

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

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How to Be Preppy After 30 Without Looking Ridiculous

Go Beyond Traditional Preppy

Don’t be tempted to grab the first piece that screams collegiate or university paraphernalia. Instead, focus on more sophisticated pieces that will give a nod to the look without overtly replicating it. 

If you want to incorporate plaid, don’t reach for a shirt. Instead, look for a casual blazer in the print. The same goes for any sort of preppy motif. Aim for more adult and modern silhouettes.

Level Up Your Preppy Style

To achieve the above point, you need to put aside the story of the college boy and instead take inspiration from the yuppies who ruled the work wardrobe and from the most elegant yacht parties you can imagine. 

For this, paying attention to the accessories and achieving a good balance between vintage and modern is key.

Embrace Fancy Sweaters

This does not mean you should stop using patterns, embroidery, or fun images on your clothes. We are not referring to plain sweaters exclusively. You may have the Ralph Lauren bear on your chest, but this does not mean it tastes bad. 

What we mean here is that you should leave out of my looks all those models with hoodies, frayed, loose, or that are slang. Not because they are ugly, but because they're not on the same channel as the style you’re pursuing at your age, where professional and personal life mix.

Skip the Skinny Pants

Another way to look consistent with the lifestyle of an adult man who loves a preppy style is to stop wearing skinny or slim pants. 

The most sophisticated and functional thing will always be to have straight models that do not squeeze your body too much. In addition to style, it has been shown that skinny pants and jeans can harm our health.

Go for More Sober Hairstyles

You don’t want to mimic the cuts or hairstyles you wore ten years ago when it was preppy to bang my bangs over my forehead, lift a giant toupee to the front of my head, or gel my curls in the back. 

It is time to choose the most classic and sober styles a man can have. This way, you will look very attractive without looking like a guy of 30 years or more who combs his hair just like in high school.

Choose Casual Sneakers

Don’t limit yourself to dress shoes or loafers; don’t exclude sneakers from the equation. 

Wear casual sneakers in a solid color to avoid looking out of place or like a guy who doesn’t know anything about anything. They can be white, but they will also work for you in brown and blue or with pastel shades.

Avoid Overloading Your Look  

Do not exaggerate the elements of your look. Don’t put all my preppy clothes together at once. The elegance of this look is always achieved by moderating classic pieces with more statement pieces. If you wear a plaid suit, combine it with a tie, a coat, and socks that do not share the same texture.

How to Be a Preppy Man in the Menswear Age of Chaos

Fashion trends come and go, but preppy style seems to have been...well, forever. Or so it’s seemed over the past 20-odd years: from Gossip Girl’s Nate Archibald to Hailey Bieber and Vampire Weekend to Saltburn’s Felix Catton, it feels like we’ve never been too far from the coronation of a new moneyed supreme.

​​Modern Preppy

Here’s the thing with preppy style: it hasn’t really changed all that much since its original ‘80s heyday until now. Ralph Lauren polos and pale-toned J. Crew sweaters are all well and good (that stuff is eternally solid), but in the 2020s, preppy style is increasingly leaning into its wilder side. 

Think shredded cardigans, shouty skirts, and oddball reinterpretations of OG preppy brands like Lacoste. Welcome to prep’s new golden, chaotic age.

What Is Preppy Style, Anyway?

The term preppy comes from preparatory school, the American name for a posh public school designed to prepare its students for attendance at an outrageously priced college. 

The term preparatory school itself originated in England, and preppy subculture has a lot of roots here, too, but for the sake of explanation, we're focusing on America, where the best kind of prep comes from.

Preppy Lifestyle

For years, preppy wasn’t just a look but a lifestyle: it referred to someone from a wealthy family who attended all the suitable social events – think polo tournaments, regattas, debutante balls – spoke correctly, and went on holidays in costly places. 

Until the ‘80s, to be preppy was old money, well-connected, and, in all likelihood, white. The dress code included lightweight seersucker suits, cable-knit jumpers, and polo shirts—neat attire that bridged the gap between buttoned-up high society and sporty youthfulness.

How Did Preppy Style Get to Where It Is Today?

Preppy style sailed along in its coastal elite enclaves throughout the 20th century until the ‘80s, when the look exploded into the mainstream thanks to The Official Preppy Handbook, a piece of satire on how to attain the preppy lifestyle. It was hugely influential. 

The book's success coincided with that of Ralph Lauren and the founding of J. Crew, both of which focused on the preppy; together, brands like these helped pull the style out of university campuses and into the high street.

Preppy Reinvention

The ‘80s preppy is now seen as a pure expression of the style. Still, even then, outsider designers were reinterpreting traditional preppy codes: Lauren’s name is synonymous with preppy clothes, but he was the son of Jewish immigrants—hardly the typical WASP archetype associated with rugby tops and boat shoes. 

The preppy craze trailed off through the 90s, but it has flooded culture ever since its heyday. The classic 1999 thriller The Talented Mr Ripley, starring Jude Law and Matt Damon, plays on the aspirational nature of preppy dressing – Damon’s character, Tom Ripley, is mistaken for someone more affluent because of a blazer he’s borrowed – while Gossip Girl contrasted the clean-cut preppy style of its lead characters with their sordid, soapy lifestyles.

Modern Preppy

When Vampire Weekend released its first album in 2008, it was criticized for its preppy look, even though it contrasted its polos and boat shoes with lyrics that referenced Jewish New Yorker identity and Ralph Lauren style. 

More recently, Tyler, the Creator, and Hailey Bieber have been repping remixed versions of the preppy look, mixing knit vests and crisp chinos with exaggerated silhouettes and mad prints.

How to Dress Preppy in 2024

If you’re looking to incorporate preppy style into your look, let the ethos of Tyler and Bieber guide you: unless you’re looking to get into a golf club, there’s no need to go full trad with it.

Many brands are now incorporating preppy signatures into their clothes without any of the old baggage. London-based label Charles Jeffery Loverboy, known for its punchy knitwear, makes preppy-adjacent pieces that look like they’ve been defaced.

Chaotic Preppy

CJL’s inside-out-looking Guddle knits invert the classic clean feeling of the preppy look, instead turning a symbol of neatness into something weird and chaotic. The red heart-patterned Guddle jumper, in particular, feels like a fresh new take on the preppy argyle sweater. 

Similarly bright are Chopova Lowena’s deconstructed pleated skirts, which look like punky, anarchic descendants of tennis club kit.

Subtle Preppy

For a preppy look that’s still fun but decidedly less flashy, London-based designer S. S. Daley has introduced a subtle twist. Daley’s knits channel WASP (shorthand for ‘white Anglo Saxon protestant’) affability with an edge, incorporating slashed details and slackly tied ribbons into bold striped jumpers and turtlenecks or contrasting a mohair diamond pattern against rugged red lambswool on his Jupp Diamond vest. 

Daley’s signature, the ultra-wide-legged Alexander trousers, also exaggeratedly channel a preppy look and would look great paired with a simple polo from Maryam Nassir Zadeh or Jacquemus or a slightly louder polo from PAM or Wales Bonner. 

Modern Classics

And if you still feel beholden to blue-chip preppy labels, feel included. Denim Tears’ Pan-African flag sweaters, available in various colors and styles, reinterpret the Ralph Lauren American flag sweater while tapping into founder and creative director Tremaine Emory’s interest in African-American history and iconography. 

Lacoste has been ramping up its collaboration game of late. Its crossover with Tyler, the Creator’s Le Fleur label, splashes his signature sky blues and pale pinks onto Lacoste's standard issue.

Modern Variations

And then there's a link-up with Comme des Garçons. Conversely, the shirt features simple menswear silhouettes emblazoned with oversized or off-kilter versions of Lacoste’s instantly recognizable crocodile logo.

There’s no one way to embody preppy style in 2024. Far removed from the prim-and-proper vibe of a ‘50s university campus, modern prep is about nodding to The Heritage while tapping into menswear's wild, endless possibilities; it might not precisely capture the Gossip Girl look – but it’s way more fun.

Color Analysis by WhatColors

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 color with our WhatColors nail color generator. 

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

The Key to Dress Unpretentiously Preppy

Cozy Up with Sweaters

Sweaters are that cozy garment you spend hours snuggling up in at the library (or so it appears). This collegiate staple is comfortable, versatile, and works on the go. Crewnecks and V-necks can be layered over button-downs to show off the quintessential preppy collar. What sets preppy sweaters apart from athletic ones is the difference in fabric.

Sweater Options

Ivy-inspired preppy sweaters are woven with cotton, wool, and cashmere, while other sweaters may be made with a polyester and nylon blend. You can have fun with patterns like argyle and cable-knit, but try limiting mixing and matching. Prep school style, rooted in early 20th-century New England fashion, is tame. 

You may have seen badminton enthusiasts and Wolf of Wallstreet characters tying sweaters around their necks and waists. We suggest you pass on this one. It looks pompous, like a Pomeranian wearing a bowtie.

Collared Shirts Are a Must

The collar is a preppy hallmark, whether on a Polo, an Oxford button-down, or a seersucker shirt. Polos, created by the Brooks Brothers’ early president, are adapted versions of 19th-century athletic shirts worn by polo players. 

These shirts had buttoned-down collars to prevent them from flapping in the wind. And thus, the intelligent, casual, sporty polo shirt was born. Wear polos in pastel colors, even in striped prints, but do not pop the collar. You won’t look like a colonial general or a fancy Britishman. You will, however, look like a symbolic tool.

Chinos for a Polished Look

The gist of preppy style is that it’s somewhat formal and elevated but not Monopoly-man chic. This Ivy-inspired aesthetic hits a healthy balance between student and professional for a bright everyday look. Chinos are the perfect pants to fit this mold. They are straight-fit pants made from lightweight cotton with a tighter fabric weave than khakis.

Due to their polished fabric finish and slimmer fit, these pants are a class of formal, casual wear. Chinos are typically beige, navy, or blue, but feel free to go pastel and try bold colors. We’re going to discourage full-on Go-To Hell Pants, though. For a presentable daily look, you don’t want “guffawing on astroturf while wearing a peacock feather hat” vibes.

Blazers Are Your Best Friend

As Tommy Hilfiger, the man himself, once said, a navy blue blazer can take you from office meetings to dinner out with friends. This prep-style staple can be dressed up, dressed down, and accessorized. 

The right-fit blazer should hang straight down without being too restrictive or oversized. Here’s a mashup we’re excited about: the sweater blazer. Comfy, huggable material with lapels to look mind-twistingly casual, but casual? Yeh.

Accessorize to Add Flair

It is our favorite component of the prep style. Long live ties, bowties, pocket squares, and lapel pins. Accessories add a flair of color and general “tricked outness,” to this overall conservative look. Skinny ties and bowties can be worn with a blazer, a V-neck sweater, or an oxford button-down. 

Go for fun prints. A modest dose of bold design will allude to your keen eye and good taste, emphasis on “modest.” Try pairing an If the Shoe Fits Bow Tie with a pastel shirt. Since we’re talking preppy style and not full-blown formalwear, you don’t need the whole gamut of accessories at once. If you’re wearing a pocket square, consider going tieless.

Shoes Can Make or Break Your Look

You can’t nail prep style without a pair of semi-formal, nautical, sporty, shoes. Sperrys were invented when an avid boater, Paul Sperry, needed shoes to prevent slipping on his watercraft. 

He cut patterns into his shoe bottoms for more grip, and voila: we have stylish boat shoes, a preppy man’s everywhere footwear.

Sweater Options

Protip: Never let your socks show when wearing boat shoes. 

You should opt for no-show socks. The Oxford shoe is another closed-toe lace-up shoe that looks smart as hell. It is characterized by closed lacing and can be dressed up or down. Remember the modest, bold rule? Try pairing Oxfords with some neon laces.

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43 Must-Know Preppy Clothing Brands

1. J.Crew: The Preppy Pioneer

J.Crew is a classic preppy brand that has been around since 1983. Known for its timeless style, J.Crew is the go-to shop for anyone looking to achieve that quintessential preppy look. The classic brand has a wide selection of clothes, including:

• Crisp button-down shirts

• Colorful cashmere sweaters

• Tailored trousers

• Preppy blazers

If you’re looking for a trendy summer wardrobe, J.Crew also has a variety of dresses, skirts, and shorts that will help you put together the perfect coastal look.

2. Tommy Hilfiger: The Iconic Preppy Brand

Tommy Hilfiger is another iconic preppy brand that has been around since 1985. The classic label is known for its colorful, American style that perfectly blends traditional and modern design. Tommy Hilfiger is the perfect brand to shop for if you’re looking for stylish preppy clothes with a fun twist.

3. Abercrombie & Fitch: The Retro Preppy Brand

Abercrombie & Fitch is a classic American brand creating timeless styles since 1892. The brand has undergone many phases over the years, but its current aesthetic features a mix of retro and modern styles that epitomize coastal, preppy living. If you’re looking for comfortable and classy pieces to create the perfect preppy uniform, Abercrombie & Fitch is a great place to start.

4. Tory Burch: The Luxurious Preppy Brand

Tory Burch is a luxurious preppy brand that offers ready-to-wear pieces and accessories that are perfect for achieving the preppy look. The brand is known for its classic, colorful, and preppy aesthetic that appeals to women of all ages.

5. Kate Spade: The Playful Preppy Brand

Kate Spade is a great place to explore for preppy and pretty clothing. The brand was founded by Kate and Andy Spade in 1993 to offer high-end bags at an affordable price point. 

Since its inception, Kate Spade has focused on providing pieces with an optimistic and feminine spirit.

6. Lilly Pulitzer: The Queen of Preppy Fashion

Lilly Pulitzer should be your go-to brand for timelessly chic preppy clothes. This iconic fashion brand blossomed after Palm Beach socialite Lilly Pulitzer started her juice stand in the 1950s. After a few lemonade spills on her dress, the late Lilly collaborated with a dressmaker to create spill-proof linen dresses with a cotton-lined design. 

And the result? The first Lilly shift dress was born. This dress caught the attention of fashion lovers in Palm Springs to the point where every fashionable woman wanted a dress. Lilly Pulitzer also gained more success after Jackie Kennedy was featured on the front cover of Life Magazine wearing a Lilly dress.

Lilly Pulitzer

Fast-forward to more than 50 years later, and Lilly Pulitzer is still a fan favorite among fashionistas who love clothes with a charming and timeless allure. The shift dresses are the bestsellers, but you will also fall in love with many more styles. This includes:

• Ruffle tops

• Relaxed button-down shirts

• Fun accessories

Every piece is guaranteed to add some joy and femininity to your closet.

7. Vineyard Vines: The Premier Preppy Brand

Vineyard Vines began in 1998 after two brothers, Shep and Ian Murray, grew tired of working at their office jobs. They set out to exchange their mundane office lives for fun outdoor adventures. The brothers decided to share their love for the American dream and Martha’s Vineyard in their fashion brand (hence the name Vineyard Vines).

Vineyard Vines

The brand is defined by the preppy ethos of the summer and the quintessential East Coast lifestyle. It also targets anyone trying to live the good life. Vineyard Vines’ collections include:

• Straw tote bags

• Cashmere cardigans

• Silk shirt dresses

• More pieces that embody timeless elegance and coastal charm

Wear the clothing to seaside escapades, a Kentucky derby, or summer weddings.

8. Sperry: The Boat Shoe Brand

Sperry embodies a fun and elegant spirit and makes waves in the fashion industry with its iconic boat shoes. The brand was founded in 1935 when the founder, Paul Sperry, fell overboard from a boat. This accident inspired him to make the world’s first slip-resistant deck shoes to help him continue doing what he loved the most: sailing! 

Eventually, in 1946, new Sperry styles were launched, and they could be used beyond the sea for everyday usage like playing tennis and leisure. So, if you’re hunting for preppy footwear, Sperry should be your go-to destination for the finest boat shoes. Boat shoes with floral motifs, leather materials, and mule finishes come in different styles, colors, and finishes.

9. Lacoste: The Original Preppy Brand

Have you ever wondered who was behind the idea of the shirts and clothes with the crocodile logo? Enter René Lacoste. The legendary Tennis champion René Lacoste invented the world’s first short-sleeved polo shirt in a breathable fabric to make playing tennis more comfortable. 

This shirt gave him a light-bulb moment to launch the brand Lacoste. He launched the brand with the principles of breaking fashion rules while keeping it classy and elegant. Inspired by his fearless skills on the court, Lacoste earned the playful nickname “the crocodile.” This nickname sparked the idea of making the crocodile his brand's logo. 

The iconic crocodile is synonymous with effortless elegance and athletic chic style. Lacoste has all the elegant clothing items and must-haves to meet your preppy fashion needs. You will find everything from:

• Timeless sweater vests

• Monogram varsity jackets

• Polo shirts

• Tapered checkered pants

• Canvas tote bags

10. Talbots: The Classic Preppy Brand

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

Talbots is brimming with the best preppy clothes, from polished casual pieces like:

• Linen blazers

• Tweed collarless jackets

• V-neck sweaters

• Great fancy dresses 

11. Southern Tide: The Coastal Preppy Brand

Southern Tide is for the fashion-forward woman who loves a preppy, southern style. The brand was founded in 2006 in South Carolina. Its first product, the Skipjack polos, put it on the fashion map. 

The polos became a hit in fashion because of their:

• Fit

• Design

• Comfort

Southern Tide

The brand later added clothing collections for tennis matches, outdoor adventures, and many other occasions. So, whether you have a fancy dinner date or want to go on a casual outing, Southern Tide has a great selection of high-quality and timeless coastal pieces. 

Think stripe dresses, wide-leg pants, twill shorts, and crewneck t-shirts. What’s also great about Southern Tide is its unique collegiate collection, which gives you endless access to the best:

• Polo shirts

• Button-down shirts

12. Brooks Brothers: The Epitome of Preppy Style

Brooks Brothers is the epitome of preppy style. The brand was founded in 1818 to design classic American styles. It has been a fan favorite among 39 American presidents and dapper Ivy League gentlemen. 

The brand isn’t only a men’s brand. Brooks Brothers has expanded its offering to women. The legendary brand offers clothes that fall under the preppy style. You will find everything from chic suit separates to:

• Linen dresses

• Polished polos

13. Rowing Blazers: The Cool New Preppy Brand

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

• Bright colors

• Unique touches

So, if you’re searching for preppy blazers with streetwear and sporty influences, Rowing Blazers is your brand. Beyond the blazers, this brand also has a great selection of:

• Polo t-shirts

• Knits

• Leisurewear

14. Alice + Olivia: The Whimsical Preppy Brand

Alice + Olivia was born from Stacey Benet’s love for vintage and feminine styles. This A-list favorite brand has a great selection of whimsical yet classy designs to complete your preppy wardrobe. 

Some bestseller items are denim dresses, wide-leg pants, and midi dresses—trust me, you will not be disappointed with their chic designs.

15. Land’s End: The Family-Friendly Preppy Brand

In 1963, Land’s End was built on the principles of crafting high-quality clothing pieces for the entire family. The brand combines elegance and functional designs to create timeless, comfortable pieces. 

The goal is to make their clothes so soft and easy to wear that they feel like they are experiencing “Sunday comfort” daily. With the endless selection of blazers, coats, fleece tops, chino pants, and more, you will quickly assemble the best preppy looks!

16. Sporty & Rich: The Ivy League Aesthetic

Want to look like a sporty and rich Ivy League student? Check out this timeless brand. It was established from a dreamy mood board about life’s beautiful moments, mixing past inspirations with modern elegance. 

The brand evolved from a chic print magazine to a preppy fashion brand that offers simple yet elegant styles that outlast the fashion calendar.

17. Wilfred: The Exclusive Preppy Brand

Wilfred is an exclusive brand by the iconic fashion label Aritzia. What we love about Wilfred is the endless option of feminine and flattering pieces. The pants have a chic appeal, the trench coats are timeless, and the tops exude a romantic flair.

18. Barbour: The Classic British Brand

John Barbour established his namesake label in 1894. His most popular design for the brand is the wax cotton jacket, which was launched in 1936. 

Due to its style and durability, it became a go-to jacket for motorcycle riders. The luxury English brand has other great pieces that are exceptionally made and will stand the test of time. Barbour has a good collection of:

• Cardigans

• Jackets

• Tailored pants

• Boots

19. Hunter Boots: The Preppy Rain Boot

You’ve probably seen royals and Hollywood celebrities sport Hunter Boots. This famous brand has amazing boots that will go with any preppy outfit. 

They can accompany jeans and a button-down blazer, a flowy wrap dress, or even a trench coat and jeans; endless styling possibilities exist.

20. J.Mclaughlin: The Timeless Preppy Brand

Immerse yourself in the stylish and preppy world of J. McLaughlin. This brand was launched in 1977 by two brothers, Jay and Kevin, to craft classic American sportswear apparel with a modern twist. J. Mclaughlin prioritizes timeless style over fleeting trends. 

The J brand is all about designing clothes that are not pretentious. You will not have a dull moment scrolling through the J. Mclaughlin website. The brand has fancy pieces in signature prints that are great for formal occasions and casual days, such as:

• Long-sleeve tops

• Blazers

• Tailored shorts

• Polished accessories

21. Sail to Sable: The Coastal Resort Wear Brand

In 2012, Jennifer Stocker traded her publishing career for a fashion venture. She started Sail to Sable out of a passion for:

• Classic silhouettes

• Statement prints

• Dreamy summer adventures on the East Coast

Jennifer’s female-led brand curates resort wear that effortlessly elevates everyday style with a preppy, coastal charm.

22. Ted Baker: The Effortlessly Preppy Brand

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

• Tote bags

• Romantic floral dresses

• Drape-neck tops

• Slingback pumps

23. Banana Republic: The Preppy Basic Brand

Banana Republic has no shortage of preppy clothes to take your style from bland to preppy in seconds. Mel and Patricia Ziegler founded the brand in 1978 out of a spirit of adventure. You can find everything from:

• Blazers

• Trench coats

• Sweaters

• More wardrobe classics

24. Ralph Lauren: The Father of Preppy Style

This list of preppy clothing brands wouldn’t be complete without Ralph Lauren. For over 50 years, Ralph Lauren has designed clothes that tell a story of authenticity and timeless elegance. You will find polo shirts, jackets, and button-down shirts that blend sophistication with allure.

25. Michael Kors: The Classy Preppy Brand

Michael Kors is the epitome of chic and accessible luxury. American fashion designer Michael Kors started his namesake brand in 1981. 

For over 40 years, Michael Kors has always delivered the most fashionable pieces, which is why this brand should be your go-to for:

• Polished accessories

• Garments

26. Levi Strauss & Co.: The Denim Brand

Every preppy wardrobe needs a stylish, classy, and reliable pair of jeans. After all, jeans are the building blocks of most preppy outfits, so Levis is an excellent brand to check out. Levis, a brand that has shaped fashion and popular culture, was founded in 1853 by Levis Strauss, an immigrant from Bavaria.

Levi Strauss

Setting up shop in San Fransisco, California, during the California Gold Rush, he identified a need for durable workwear. This led to a collaboration with tailor Jacob Davis, resulting in the invention of the iconic Blue Jeans in 1873. 

From being exclusively worn by gold miners, these jeans soon found favor with Hollywood starlets like Marilyn Monroe, marking the beginning of their iconic journey through popular culture.

27. Coach: The Accessory Brand

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

28. Guess: The Preppy Vintage Brand

Guess was founded by the Marciano brothers in 1981. They swapped their love for the South of France for the American dream. The brothers used their European influence to inject an elegant flair into denim. 

The result? The iconic Menlyn jeans were born. The brand has expanded beyond denim to:

• Dresses

• Handbags

29. Nautica: The Nautical Preppy Brand

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

30. Hugo Boss: The Preppy Sophisticated Brand

Hugo Boss is not just a preppy brand for gentlemen. This German brand also has great pieces for women. You will be satisfied with the wide selection of modern and classy pieces!

31. Cole Haan: The Preppy Footwear Brand

You might not have heard of Cole Haan, but you will want to shop there when you go through the brand's timeless footwear. Cole Haan was established in 1928 to offer excellent:

• Craftsmanship

• Comfort

• Design

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

32. Loewe: The High-End Preppy Brand

This Spanish luxury brand was founded in Madrid in 1846. Its tone is chic and classic, with influences from art. So, if you need luxurious items for your preppy closet, Loewe should be your one-stop shop for the perfect clothing. 

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

33. Mango: The Affordable Preppy Brand

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

• Sweaters

• Loafers

• Classic sunglasses

34. River Island: The British Preppy Brand

Another brand to keep on your fashion radar is River Island. This iconic British high-street brand, founded in 1959, is inspired by heritage styles and modern influences. 

The brand offers classic silhouettes that will perfectly align with your preppy style. These include:

• Intelligent blazers

• Tailored pants

• Button-down shirts

35. Club Monaco: The Preppy Basic Brand

Since 1985, the Canadian brand Club Monaco has been focused on creating better basics. The brand is committed to creating effortlessly chic classics to make your life easier. So, if you need to stock up on preppy basics, Club Monaco is calling your name.

36. Frank and Oak: The Eco-Friendly Preppy Brand

Under-the-radar brand Frank and Oak was founded in 2012 to inspire better living by designing eco-conscious clothes. It’s a great brand to shop from if you’re looking for ethically made preppy clothes. 

Some of Frank and Oak's most popular items are:

• Bermuda shorts

• Striped bubble cardigans

• Relaxed blazers

• Straight-leg jeans

37. L.L.Bean: The Outdoor Preppy Brand

Need classic outdoor outfits? Look no further than L.L. Bean. Leon Leonwood Bean started this brand in 1912 to deliver exceptionally crafted and timeless outdoor clothes. The brand offers everything from insulated jackets to:

• Sweaters

• Sandals

• Jeans

38. Gap: The Classic Preppy Brand

You can always depend on Gap for the best wardrobe staples to build your preppy wardrobe. The brand was founded in 1959 to make finding the perfect pair of jeans easier. 

More than 50 years later, Gap is not only the place to find a good pair of jeans; it’s also the go-to shop for:

• Classic white tees

• Sweaters

• Cardigans

• Shirts

39. LOFT: The Girly Preppy Brand

Get ready to be obsessed with the modern and feminine pieces at LOFT. This brand has everything you need to create that:

• Effortless

• Preppy

• Girly style

Loft offers:

• Spring tweed jackets

• Striped poplin dresses

• Rugby collared sweaters

• Charming clothes

40. Draper James: The Celebrity Preppy Brand

If you’re a fan of Reese Witherspoon, you’ll love her clothing line. Most celebrity clothing lines miss the mark, but Draper James has some lovely pieces. 

Classic prints like florals and checkpoints are a prominent theme in Draper James’ collections, which is great if you’re looking for preppy clothes with a feminine touch.

41. Dudley Stephens: The Sustainable Preppy Brand

Step up your style with Dudley Stephens, a women-led brand that caters to the modern woman’s preference for classic styles over fashion trends. 

Dudley Stephens is committed to sustainability, crafting pieces that stand the test of time in recycled performance fabrics. From turtlenecks to pullovers, shorts, and more, you will surely find a piece that speaks to your classic style.

42. Hill House Home: The Preppy Home Brand

Hill House Home should be the brand to explore for preppy clothes! The brand prides itself on celebrating life by offering exceptionally quality classic styles. Experience the elegance of Hill House Home, a brand that embodies the preppy vibe with its elegant yet simple designs. 

Picture yourself in their pretty puff-sleeve dresses, a style that instantly transports you to the Hamptons. And don’t forget to check out their cool accessories, perfect for adding a touch of spice to your preppy outfits.

43. Tuckernuck: The Preppy Collective

The last preppy clothing brand to know is Tuckernuck. There is a lot to love about this fashion retailer. Tickernuck has the best brands that offer effortlessly fresh styles, such as:

• Classic ballet flats

• Raffia tote bags

• Flowy dresses

• Polo shirts

• Tweed dresses

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