As summer winds down and the air turns crisp, we all want our preppy aesthetic to be as cute and cozy as possible. Yet, as we transition between seasons, it can be challenging to know just what to wear. Amid this wardrobe uncertainty, preppy outfits have become a go-to for Fall. Outfitted in preppy styles, you can attend your upcoming outdoor gathering in style and also keep warm in the process. If you want to learn more about building a versatile Fall wardrobe with preppy outfits, you’ve come to the right place. This blog will help you elevate your personal style with these classic yet timeless looks.

WhatColors' AI personal color analysis app can help you achieve your goals of building a versatile Fall wardrobe and elevating your personal style. You can easily choose the right tones to incorporate into your preppy outfits for the season by identifying the colors that complement your unique features.

Table of Contents

• What Is a Preppy Outfit?

• How To Dress The Modern Preppy Way

• How Do You Know You're Preppy?

• 7 Preppy Outfit Staples for Women You Need in Your Closet

• 8 Key Pieces For Men’s Preppy Style

• 15 Preppy Outfits That'll Make You Feel Like "Gossip Girl" IRL

• How to Create the Perfect Men’s Preppy Outfits

• 4 Ways to Look Preppy on a Budget

• What’s the Difference Between Preppy and Classy?

• The Best 24 Preppy Clothing Brands (And Why You Should Wear Them)

• Try AI Personal Color Analysis For Free Today

What Is a Preppy Outfit?

To picture preppy style, imagine what a college student might wear to an elite Ivy League school. This is the style you would expect to find in the cast of Gossip Girl. Preppy outfits incorporate classic pieces you would associate with academia, like:

• Cardigans

• Blazers

• Pleated skirts
  
  

But there’s more to this fashion trend than simply embracing the academic aesthetic. The preppy style evolved from old-school students who attended posh schools. While wearing their attire, these students engaged in academic pursuits and athletic activities such as tennis and golf. Contemporary preppy ensembles often incorporate elements from both:

• Scholarly 

• Sporting aesthetics
  
  

The Evolution of Preppy Style

The preppy style has a rich history rooted in Ivy League fashion. Its origins can be traced back to the 19th century when the upper class began to sport clothing made for rowing and other water sports. As the popularity of these activities grew, so did the demand for their associated garments. 

By the early 20th century, the elite had taken to wearing these outfits at social gatherings and country clubs. The look eventually made its way to college campuses, where students began to adopt the style as part of their school uniforms. Over the years, the aesthetic has evolved but has remained true to its roots. It draws heavily from vintage fashion and has been revived by the cyclical nature of trends.

Icons and Influences 

Cultural icons and influences have significantly shaped preppy style over time, transforming it from a simple dress code into a fashion icon. Among the iconic figures who have helped define this style are personalities like John F. Kennedy, who had an impeccable and casual look characterized by:

• Blazers

• Striped shirts

• Chinos
  
  

His effortless elegance has inspired entire generations to emulate his preppy style. Other historical figures who have embodied the spirit of preppy style include Ralph Lauren, known for bringing Ivy League style into mainstream fashion with his eponymous brand, and Jacqueline Kennedy Onassis, who popularized the yachting and polo look, complete with loafers and straw hats. Films like The Great Gatsby and Dead Poets Society have helped spread the preppy aesthetic, showcasing characters with classic elegance and a love for the outdoors. 

Novels such as The Catcher in the Rye by J.D. Salinger and Excellent Sheep by William Deresiewicz have also provided a rich and detailed portrayal of American educational institutions' lifestyles and typical attire, influencing the public's perception of preppy style.

Distinctive Features of Preppy Style

One of the most noticeable traits of the preppy style is its clean and polished clothing, characterized by:

• Simplicity

• Refinement
  
  

Preppy garments are usually well-structured and made from high-quality materials, reflecting an effortless sense of elegance. Tennis socks are another distinctive element of preppy style, known for their clean and sporty aesthetic. Originally adopted in elite school environments and sports clubs, these socks combine comfort and functionality with casual elegance.

Preppy Footwear

Often paired with loafers, boat shoes, or sneakers, they add refined and polished detail to the outfit. Neutral or striped colors, typical of preppy style, enhance their classic appeal. Bright colors are another key element of preppy style, manifested through a vibrant and eye-catching color palette. 

Pastel tones and bright shades of red, blue, green, and yellow often add liveliness and cheerfulness to preppy outfits, giving them a joyful and summery feel. Stripes and checks are recurring patterns in preppy style, adding visual interest and a sense of dynamism to the clothing.

Preppy Fabrics

Stripes can be found on shirts, sweaters, and pants, while check patterns are commonly used for blazers, vests, and ties, creating a sophisticated and refined look. Traditional fabrics are another distinctive feature of the preppy style, which relies on high-quality and durable materials. Cotton, linen, and wool are commonly used in preppy clothing, providing:

• Comfort

• Longevity

• Timeless elegance
  
  

Rules to Follow for Preppy Style

Embracing preppy style in your everyday wardrobe can be a fun and versatile way to express your style with a touch of elegance and refinement. Here are some tips: 

Choose Classic Clothing Pieces

Focus on clean and well-structured clothing pieces, such as polo shirts, button-down shirts, chinos, and blazers. Opt for classic and neutral colors like:

• White

• Navy blue

• Khaki green

• Burgundy, which are characteristic of the preppy style
  
  

Incorporate Typical Preppy Patterns

Add a touch of interest to your look with classic preppy patterns such as:

• Stripes

• Checks

• Tartan

• Houndstooth
  
  

To add a lively touch to your outfit, you can wear striped sweaters, checked shirts, or pants with houndstooth patterns. 

Play with Accessories

Accessories are a key element of preppy style. Opt for braided leather belts, loafers or boat shoes, aviator sunglasses, and classic watches. A scarf or lightweight shawl can also add a pop of color. 

Experiment with Personal Style

Even though preppy style has well-defined guidelines, don’t be afraid to experiment and add your personal touch. Play with color combinations and details to create unique outfits that reflect your personality and individual style. 

Pairing with Socks

Solid or ribbed socks are a perfect complement to the preppy style. Choose socks in neutral tones like navy blue, gray, or beige for a classic look, or go for colorful socks to add a touch of vibrancy. Ensure the socks are long enough to cover your skin when wearing trousers or shorts.

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How To Dress The Modern Preppy Way

A Brief History Of Preppy Style

The preppy aesthetic originates from British college rowing clubs in the early 20th century. Ivy League culture has also heavily influenced The modern preppy look, especially during the 1950s and 60s. At its core, preppy style conveys an image of wealth and privilege and is characterized by a fusion of:

• Varsity nostalgia

• Casual tailoring

• Vintage-inspired sportswear
  
  

Preppy Revival

The look is slightly nerdy, making it easy to mix with many elements of a modern wardrobe. The preppy style has recently returned to mainstream fashion, thanks partly to Alessandro Michele at Gucci, who has interpreted his maximalist version. Cult streetwear brands such as Aimé Leon Dore have further propelled the look to a diverse global audience. 

To get the preppy look right, you need to dig into its origins to understand how all elements tie together.

What Is Preppy Style?

Although we associate the genesis of today’s preppy style with the campuses of Ivy League universities in the 1950s, its true origins can be traced back to the collegiate rowing clubs of mid-19th-century England, where oarsmen wore brightly colored jackets to be discerned by the crowd on the river banks. Later, students attending social functions would wear their rowing blazers in youthful sartorial rebellion.

Preppy Origins

The blazers were often striped to differentiate one club from another. It wasn’t until the early part of the 20th century that the look caught on with university peers across the Atlantic. Still, by the 1950s, the ownership had been wrested away from Oxbridge and was creatively evolving in the elite corridors of the Ivy League. 

It symbolized moneyed, well-heeled, upper-class privilege and was famously parodied in Lisa Birnbach’s seminal books, The Official Preppy Handbook and True Prep.

Preppy Sportswear

The sporting influence did not get lost 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 vibrant patterns such as Madras check to differentiate themselves from the charcoal suits of the cubicle drones of white-collar America.

How The Preppy Aesthetic Evolved

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 20th-century menswear movements, it has 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.

Preppy Modernity

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 is wrapped up in its diversity and versatility, giving us any number of ways to pull off the look.

How To Dress Preppy

Stripes

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 have the collar peeping out of a cotton sweatshirt on the other. Think pastel stripes in the summer, while in the cold months, opt for darker shades with greater contrast.

Varsity Jacket

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

Rugby Shirt

A key piece in the preppy arsenal is the heavy cotton rugby shirt, with its requisite color-blocked panels and contrast soft-rolled white collar. Great as a way to dress down some separates, the rugby shirt is the perfect mixture of collegiate sports style and casual off-duty comfort.

It’s also a great way to inject color into your look, adding a bold dimension to a navy blazer, chinos, or even a corduroy suit. Typically constructed from heavyweight cotton, it’s a good year-round piece that offers myriad styling options.

Ocbd (Oxford Cloth Button-Down)

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 in effortlessly:

• Dressing down

• Tailoring

• Elevating knitwear
  
  

Preppy Staples

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 months, nonchalantly 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.

Straight-Leg Chinos

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.

Preppy Trousers

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 below). They are the perfect casual trouser, being both lightweight and extremely versatile.

If you want to be featured on parody menswear websites, avoid the salmon pink variety and stick to the:

• Classic khaki

• Off-white

• Navy tones
  
  

Corduroy

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.

Preppy Outerwear

Corduroy jackets, sports coats, and two-piece suits easily transition 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.

Sports Coat

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).

Preppy Blazers

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

Heritage Fabrics

One of the main reasons why the preppy style has enjoyed unrivaled longevity is that it borrows classic menswear fabrics from the past and reinterprets them in a way that feels modern. 

Preppy Patterns

Heritage cloths such as tweed, herringbone, and houndstooth, as well as patterns such as Madras check or Prince of Wales check, bring plenty of vintage sophistication to a look, but can be given a creative appeal when matched with contemporary loungewear or streetwear.

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

Leather Loafers

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.

Preppy Footwear

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.

Nautical Influences

Given that the Ivy League institutions are all dotted around the US East Coast, it’s no surprise that the preppy aesthetic includes a healthy dose of nautical references, as many images of preppy poster boy JFK on his boat will testify. 

Preppy Layers

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.

Seersucker

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’ predilection 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.

Preppy Seersucker

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 flamboyant (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

• Suiting
  
  

Shawl-Collar Cardigan

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. The Aran and cable-knit jumpers are a great way to get the look. One piece of knitwear, however, jumps to the front of the preppy queue: the shawl-collar cardigan.

Cardigans have an innately nerdy appeal, but the shawl collar adds 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 with jeans and bashed-up white sneakers, and you’d do well to take your styling cues from the King of Cool.

Polo Shirts

Polo shirts were preppy fodder long before Ralph Lauren decided to embroider a polo player on his horse. Credit where credit’s due—Mr. Lauren eternalized the association and made the polo shirt preppy lore.

Preppy Polos

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 

• Loafers
  
  

As close as you’ll come to an Ivy League uniform.

Technical Pieces

Harking back to the East Coast predilection for sailing style, more technical fabrics have infiltrated the modern preppy aesthetic in recent years in the form of:

• Windbreaker jackets

• Technical blousons 

• Gilets
  
  

Preppy Outerwear

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, straight-leg chinos, and Sperrys is about as off-duty preppy as possible.

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How Do You Know You're Preppy?

The preppy style has a long-standing affinity for monograms. A monogram is a letter or letters, often decorative, representing the initials of a name. Preppy people don't just like monograms; they love them. They want them on everything from their stationary to their towels and, yes, even their clothing. 

Monograms are a sign of classic, understated, and personalized style. To make a prep's day, you can gift them a vintage monogrammed item.

Do You Collect Ivy League Sweatshirts?

The preppy aesthetic has roots in the Ivy League and other elite Northeastern schools. As a result, many preppy outfits incorporate college logo sweatshirts and other clothing. If you want to impress a prep, find out what school they attended and gift them a vintage item with their alma mater's logo.

Is Your Pet A Dog?

Preppy people love dogs—not just any dogs, but specific breeds known for being friendly, intelligent, and good family pets. Examples include

• Golden retrievers

• Labs

• Spaniels

• Rerriers
  
  

In contrast, preppy folks are not fond of cats and don't dress them up in silly outfits.

Do You Prefer a Classic Cocktail Over a Sweet Fruity Drink?

Preppy people have sophisticated tastes. They enjoy classic things, whether it's music, food, or drinks. Rather than sipping on a sugary, neon-colored tropical drink, they'd much rather enjoy a dry martini or an old fashioned.

Do You Love Boating and Sailing?

Being prep is closely associated with the culture of the elite New England ocean communities. As a result, many preppy outfits will have nautical themes or resemble what one might wear for a day out on the water.

Do You Like To Dress Up?

Preppy people are often quite affluent and enjoy an array of social gatherings, from cocktail parties to charity balls. As a result, they have sophisticated tastes and prefer to dress well for such occasions.

7 Preppy Outfit Staples for Women You Need in Your Closet

1. Pretty Pleats: The Versatile Tennis Skirt

A wardrobe staple that has never steered us wrong is a tennis skirt. Hitting at about mid-thigh to show off those stems, pleated mini skirts became a frenzy in the 90s. Surprisingly, this skirt is popular even today and is a go-to pick for many fashionistas– all because of its crisp, clean pleats that evoke a quintessentially preppy look. 

Style it with a camisole or a tank top for a sporty look, or wear a polo shirt and toss a cardigan over your shoulders to bring back the iconic 90s look. Pull off your look with slingback heels, mules, or booties, or simply opt for biker boots for a cool, romantic look.

2. Pull on a Polo: The Classic Prep Shirt 

Sure, polos were aughts staple, but they gained cult status because they are a perfect blend of:

• Sophistication 

• Athleticism
  
  

It is no surprise that it is regarded as one of the famous pieces of prep clothing. Throw on a polo shirt and style it with a flowing maxi skirt. Elevate your whole look with a pair of white sneakers. Avoid the vintage Y2K-era double-layer polo-style shirt for a modern, preppy vibe. Instead, wear an oversized polo, which is far more elegant than the vintage-style polo. 

Preppy Knits

Even 70s-inspired knitted polos are a great option. They have resurfaced in popularity for a larger throwback, with modern markings such as bold color-blocking signaling novelty and overstated collars. Styling a knitted polo might seem complicated, but it isn’t. Put on high-waisted trousers with a knitted polo, and you’re all set to make a statement.

3. Try Vintage-y Cable Knit Sweater: The Cozy Essential

An easy preppy outfit that looks good on almost everyone is a cable knit sweater. So, it’s a must-have staple in your wardrobe. Combine a cable knit sweater with black jeans for an easy-breezy look. Or, pairing a hint of style with an untucked button-down shirt. After all, an untucked button-down shirt looks charming when worn under a cable knit sweater. 

Add a pleated skirt to the mix, and you’ve got a look that captures the essence of effortless coolness, the one that makes a preppy outfit a standout.

4. Striped Separates: The Patterned Must-Have

Stripes are the go-to pick for many fashionistas because they make almost any outfit interesting. Create a prep fit by matching and mixing preppy materials and patterns with stripes. For a casual workday, toss a striped button-up shirt and pair it with blue denim. 

Or, throw on striped shorts with a cable-knit v-neck sweater. Slip into a pair of metallic flats, which deliver prep but with a twist.

5. Remix a Rugby: The Cool Weather Essential 

Representing prep style at its core, a good rugby shirt looks gorgeous on almost everyone without being snobbish. It’s a versatile piece of clothing that can be styled on colder days and leisurely evenings. Aren’t these reasons enough to add a rugby shirt to your wardrobe? People often stick to jewel-tone and nautical (blue and white) color palettes for preppy aesthetic outfits. 

That doesn’t mean you cannot mix things up. Ditch the classic way of styling a rugby shirt. Instead, opt for a brightly colored shirt and pair it with matching bike shorts—a fresh take on an old favorite. Wear a waist-skimming crop or a puffy sleeve style for added flair and femininity.

6. Try Prep Sweats: Yes, You Can Wear Sweatpants

Did you know you can pull off preppy outfits with sweats? Many don’t, either, so you’re not alone. Since sweats make outfits preppy, why not give it a try? Put on your favorite sweatshirt, a T-shirt, and a blazer, and tie a crewneck sweatshirt over your shoulders. For a classic prep fashion, wear a baseball cap. 

Coming to footwear, a pair of sneakers will do a great job of elevating your look. So, go for them. The next time someone says preppy can’t be comfy, prove them wrong by pulling this look.

7. Opt for a Trouser: The Preppy Bottom

Who said trousers are just for interviews and internships? You can pull off preppy outfits with trousers because they are both formal and suitably relaxed. Chinos, corduroy, and twill pants are significant pieces in a preppy ensemble. Having any one of these can help you pull preppy aesthetic outfits in autumn or winter get-togethers and semi-formal occasions. Pair trousers with the coziest, fluffiest cardigan for a laid-back preppy vibe. 

A turtleneck sweater also looks great with trousers. Choose a shade that complements the color of your trousers. Round out your outfit with boots and a puffer jacket. 

8 Key Pieces For Men’s Preppy Style

1. Chinos — The Preppy Alternative to Jeans 

Chinos are a quintessential element of any preppy outfit. When dressing preppy, forget about jeans and focus on long, colorful pants, starting with a few classic chino colors. These include:

• Khaki

• Navy

• Light blue

• Grey
  
  

Once you’ve got those, take it a step further by adding lighter colors, such as:

• White

• Coral

• Light green 

• Light pink
  
  

Preppy Colors

These are all classy shades that will seamlessly integrate into your existing wardrobe without infringing on your style. From there, you can experiment with brighter colors to stand out but avoid anything neon or too unusual. Dress preppy for everyday wear, not to look like a catalog model.

2. Polo Shirts — The Preppy Alternative to T-Shirts

Polo shirts are a must-have for achieving a preppy look. A classic alternative to graphic t-shirts, they come in various colors and patterns to suit your taste. 

Aim for lightweight cotton options with an embroidered logo, preferably something nautical or a reference to a prestigious sport like polo. When the temperatures cool, consider swapping them out for long-sleeve rugby shirts.

3. Navy Blazers — The Preppy Statement Piece

No wardrobe is complete without a classic navy blazer. It can dress you up even when wearing the most comfortable and laid-back shorts and t-shirt. A navy blazer with brass buttons or embroidered crest can be paired with anything. Until you have the blazer, you will not have preppy look pinned down.

4. Sweaters and Cricket Jumpers — The Preppy Layering Pieces

Sweaters add both warmth and style to your preppy outfits. They can make a look seem modern or sporty. Wear it over a t-shirt with the sleeves rolled up, and you’ve got a jock look. 

Where it underneath an Oxford shirt, and you’ve got the modern Ivy League look. For cricket jumpers, plain colors or embroidery around the neckline all work.

5. Preppy Shoes — Brogues, Penny Loafers and Boat Shoes

Brogues, penny loafers, and boat shoes are all classic preppy footwear options. Rich browns or oxblood, printed leather or lace, with socks or without socks, with shorts or chinos. These shoes, like the sweatshirts, are meant to be used interchangeably to dress up or dress down.

6. Belts — The Most Versatile Preppy Accessory

Belts might not seem that exciting, but they’re the most versatile accessory in the prep world. Woven, elastic or vegetable-tanned leather belts, complete with brass buckles, sometimes lined in silk. 

Rule of thumb: No studs or widths lower than 25mm or higher than 35mm.

7. Tweed Tailoring — A Touch of English Outdoor Elegance

If you want to go the extra mile for fancy events, opt for tweed tailoring for a touch of English outdoor elegance. Look for slim but not restrictive to make your tweed look sharp while maintaining the following:

• Comfort 

• Practicality
  
  

8. Casual Ties — The Preppy Accessory to Elevate Your Look

Again, another extra step not required for all is the diagonally striped or small embroidered woolen or knitted bow or necktie. It is meant to be worn smartly and casually with:

• Chinos

• Sports coats

• Cricket jumpers

• Shirts
  
  

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15 Preppy Outfits That'll Make You Feel Like "Gossip Girl" IRL

1. Warm and Fuzzy Monograms

Monograms are a hallmark of preppy style, and this cozy sweatshirt has the perfect vintage collegiate feel. What elevates this look is the varsity letter patch. You can snag this lettered patch from any craft store and customize your pullover sweatshirt to make it your own. The H&M Grey Varsity Sweater above already has a letter patch for a no-fuss preppy look.

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 2022. 

• You'll need: MakeMeChic Plaid Skirt, $27, amazon.com 3. Vintage-y Cable Knit The combo of a red cable knit sweater and jeans is an easy preppy outfit to pull off. Grunge down the look with Docs and a trendy shoulder bag. 

• What you'll need: Fluffy Cable Crew Sweater, $48, abercrombie.com
  
  

3. Vintage-y Cable Knit

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

What you'll need: Fluffy Cable Crew Sweater, $48, abercrombie.com

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. 

What you'll need: Asset Cognac Leather Boots, $120, stevemadden.com

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. 

What you'll need: Vintage Slouchy Plaid Short, $45, urbanoutfitters.com

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 like fashion.

What you'll need: Knitted V Neck Sweater Vest, $29.99, amazon.com

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. 

What you'll need: Plaid Straight Leg Pants, $40, forever21.com

8. Plaid on Plaid

Don't be afraid to wear a monochrome look with prints. Hailey Bieber knows that plaid is practically neutral when it's in classic shades like:

• Grey

• Black

• White
  
  

What you'll need: Plaid Straight Neck Mini Dress, $28, ardene.com

9. Belts, Caps, and Bags

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

What you'll need: Faux Wool Cabby Hat, $16.90, windsorstore.com

10. Gothic Peacoat

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

What you'll need: Fulton Wool Coat, $345, marcellanyc.com

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-y concert tee

• Pants
  
  

What you'll need: Varsity Baseball Lettermen Jacket, $39, Amazon.com

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. 

What you'll need: Marisole Cardigan Dress, $191, saylor.nyc

13. Clean White Turtleneck

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

What you'll need: Pima Micro-Rib Turtleneck, $50, everlane.com

14. Updated Penny Loafers

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

What you'll need: Rate Moc Toe Loafers, $65, drschollsshoes.com

15. A Classic Varsity Sweater

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

What you'll need: V-Neck Cable Knit Wool Sweater, $132, lacoste.com

How to Create the Perfect Men’s Preppy Outfits

You must have a few key pieces in your wardrobe to create the perfect preppy outfit.

Essential Clothing Items

A few essential clothing items for a preppy outfit include:

A Well-Tailored Blazer

A blazer is a versatile piece that can be dressed up or down. For maximum wearability, choose a blazer in a neutral color like navy or gray.

Khaki Or Chino Pants

Khaki or chino pants are a staple in any preppy wardrobe. They are comfortable, stylish, and suitable for various settings.

A High-Quality Polo Shirt

A polo shirt is a preppy classic. To add color to your outfit, look for a bright pink or green one.

A Cable-Knit Sweater

A cable-knit sweater is a cozy and stylish addition to any preppy outfit. Choose a sweater in a neutral color like cream or gray for maximum versatility.

Layering for a Polished Look

Layering is essential to creating the perfect men’s preppy outfit. For a polished finish, layer a cable-knit sweater over a button-down shirt or pair a blazer with a polo shirt.

Don’t be afraid to mix and match textures, either. A wool blazer paired with a cotton polo shirt and a silk pocket square creates a sophisticated and stylish look.

Accessorizing Your Preppy Outfit

Accessorizing is an important part of creating the perfect preppy outfit. It adds a touch of personality to your ensemble and can elevate your look from ordinary to extraordinary.

A few must-have accessories that can instantly up your preppy game include:

Must-Have Accessories

• A high-quality leather belt: A leather belt is a versatile accessory that can be worn with almost any preppy outfit. Opt for a brown or black belt with a simple buckle for a classic look, or go for a braided or woven design for something more unique.

• A patterned pocket square: A pocket square is a small but impactful accessory that can add color and pattern to your outfit. Choose a pocket square in a complementary color to your shirt or tie, or go for a bold print or pattern for a statement look.

• A classic wristwatch: A wristwatch is not only a practical accessory for keeping track of time, but it can also be a stylish addition to your preppy outfit. Look for a watch with a leather or metal strap and a simple face for a timeless look.
  
  

How to Tie a Bow Tie

• For a formal preppy outfit, a bow tie is a must. While it may seem daunting to tie a bow tie, it’s quite simple once you know how. 

• Start by placing the bow tie around your neck, with the right side longer than the left. 

• Cross the right side over the left, then bring it up and over the knot. 

• Take the left side and wrap it around the knot, then bring it through the opening between the knot and your neck. 

• Adjust the bow tie until it’s even on both sides.
  
  

The Importance of Footwear

No preppy outfit is complete without the right footwear. The right shoes can tie your outfit together and take your look to the next level. A few classic shoe options that are perfect for a preppy outfit include: 

• Loafers: Loafers are a timeless shoe style that can be dressed up or down. Choose a brown or black leather pair for a classic look or a bold color or pattern for something more fun.

• Boat shoes: Boat shoes are a summer staple perfect for a preppy outfit. Look for a pair in a neutral color like navy or beige, or go for a brighter hue like yellow or red for a pop of color.

• Chukka boots: Chukka boots are a versatile shoe style that can be worn year-round. Choose a pair of brown or black suede for a classic look, or go for a bold color like green or blue for something more daring.
  
  

Dressing for Different Occasions

The preppy style can be dressed up or down to suit a range of occasions.

Casual Preppy Outfits

For a casual preppy outfit, layer a cable-knit sweater over a polo shirt and pair it with khaki pants or shorts. Boat shoes or loafers complete the look.

Semi-Formal Preppy Looks

Pair a blazer with a button-down shirt and khaki pants for a semi-formal preppy outfit. Add a patterned pocket square and loafers for a polished finish.

Preppy Attire for Special Events

A formal preppy outfit is necessary for special events such as weddings or galas. Pair a well-tailored suit with a:

• Bow tie 

• Classic leather dress shoes
  
  

4 Ways to Look Preppy on a Budget

You don’t have to spend much on clothing and accessories to look preppy. Consider these tips and tricks for dressing in the preppy style and get ready to rock this look without going broke:

1. Purchase a Few Statement Items

A statement item is typically a particularly eye-catching piece of your outfit. Statement items are unique and attract the most attention. Because these pieces stand out from the rest of your wardrobe's clothes, you only need one or two (maybe three) statement items to make a difference. 

You can then incorporate them into your capsule wardrobe for a more affordable yet fashionable preppy style.

2. Create a Preppy Capsule Wardrobe

A capsule wardrobe is a collection of interchangeable clothing items. It aims to create as many different outfits as possible with less clothing. It keeps you from buying more clothes than you can manage while saving you money. 

The key to creating a capsule wardrobe is buying versatile clothes. You can incorporate a statement piece or two, but consider how each item will go with the other clothes in your closet. For maximum mixing and matching, opt for neutrals like black, white, camel, and beige. Then, add your favorite colors with accessories.

3. Buy High-Quality Essentials

Quality over quantity, right? High-quality essentials like coats, jeans, and sneakers ensure they can withstand regular wear. Not buying the same items repeatedly can save you a good chunk of change. 

If you’re going for the preppy look, purchase some prep-inspired essentials so they’re always part of your look.

4. Grab at Least One Crisp Button-Down Oxford Shirt

A crisp button-down Oxford shirt is essential to the classic preppy style. Oxfords are long-sleeved shirts that effortlessly work as both a casual top and a dress shirt—whatever you need them to be. Just having one of these in your wardrobe will amp up your preppy style, no matter how you rock it. 

The same can be said for picking up at least one polo or other type of collared shirt. Depending on the style and colors, stripes also scream preppy style. 

What’s the Difference Between Preppy and Classy?

Preppy and classic styles share similar roots but different sartorial expressions. Both draw from traditional New England or Ivy League influences. While the classic style is polished and orderly, the preppy style is more casual and relaxed.

Defining Preppy Style: How to Identify It

The preppy style features traditional pieces with a collegiate flair. Think of the outfits you’d find in a high-end catalog for a private school. There are lots of blazers, argyle, chinos, and polo shirts, and everything is:

• Neat

• Clean

• Colorful
  
  

The overall look is smart and sophisticated but not stuffy. It’s comfortable and easy to wear as if you could wear it to class and then head out to the golf course with friends.

Defining Classic Style: How to Identify It

Classic style also features traditional pieces, but the look is more understated and less colorful than the preppy style. The outfits appear elegant and refined and are suited for a variety of occasions, including formal events.

While preppy outfits exude a youthful vibe, classic looks are timeless and never go out of style. They improve with age. Classics like trench coats, tailored blazers, and little black dresses have been around for decades and will be just as popular in another hundred years.

Comparing the Color Palettes of Preppy and Classic Styles

Preppy outfits feature bright, cheerful colors and bold patterns. The color palette often resembles a box of crayons. You’ll find many yellows, greens, pinks, and blues, especially in pastel hues.

On the other hand, classic-style outfits rely on a more muted color palette that includes earthy tones and neutral shades. While preppy looks embrace color, you could envision classic outfits in a black-and-white film.

The Best 24 Preppy Clothing Brands (And Why You Should Wear Them)

Preppy fashion is so influential that it went from 60s college students to 80s finance bros to 90s skate kids. The latter inspired ex-Supreme creative director Brendon Babenzien to found Noah, a New York label that lovingly recaptures the fusion between skatewear and preppy fashion. There’s a heavy dose of JFK-lite nautical style, plus slacks and loafers, but it’s mixed with big graphic tees and eye-popping prints. Somehow, it just works and it’s all very easy to wear.

1. Brooks Brothers

No one can deny Brooks Brothers is an American icon. Founded in 1818 in New York by Henry Sands Brooks, it introduced its first ready-to-wear suits in 1849. To give this some context, 1818 was the year the White House officially reopened after being burned in 1814 by the British in the War of 1812. 

Brooks Brothers has provided preppy clothing for the American elite (and beyond) ever since. Favored at the highest level by many US presidents, including most famously JFK, the brand is noted for its high-quality, timeless clothing. It is a true American institution.

2. J.Crew

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

Preppy Styling

In its campaign and lookbook shots, you’ll find modern pairings of sneakers with suits and brogues with jeans alongside:

• Traditional color-blocking 

• Pattern mixing
  
  

The quality is good, and the price point is reasonable.

3. Ralph Lauren

American designer Ralph Lauren (born Ralph Lifshitz) founded the Polo Ralph Lauren Corporation in 1967. 10 years later, in 1977, the company introduced the signature cotton mesh Polo shirt in various colors. Featuring the now-iconic polo player logo on the chest, the shirt became emblematic of the preppy look and put Ralph Lauren on the map. 

Lauren himself breathed the American Dream into a clothing (and other) brand, creating the embodiment of a particular lifestyle or way of life.

4. Billy Reid

Southern preppy is a niche-style tribe in the broader Americana family. It takes classic preppy fashion but gives it a slightly looser, more casual, ranch-ready flavor. Billy Reid is its patriarch, a designer highly revered in fashion circles even if he doesn’t have the mainstream clout of Lauren or Hilfiger. 

Everything you expect from the best preppy brands, especially:

• Polo shirts

• Button-downs

• Easy-wearing shorts and trousers
  
  

5. Aurelien

The quiet luxury movement borrows heavily from some understated but always sophisticated preppy fashion styles. Aurelien puts an Italian spin on it with timeless garments like knitted polos, loafers, and unstructured tailoring. 

It’s a direct-to-consumer label, offering lower prices than some designer labels it shares factories and mills with.

6. Luca Faloni

Italian menswear has long remixed the staples of preppy fashion with a touch of La dolche vita.
Think:

• Knitted polo shirts

• Unstructured blazers

• Tailored chinos
  
  

Luca Faloni does all these and more at prices lower than expected for a label 100% made in Italy. The vibe is more tailored and summery than the classic collegiate style, but the brand also weaves in hoodies and sweats – again giving a luxe touch in beautiful knitted fabrics.

7. Pelota Sporting Clothiers

British brand Pelota designs clothes for Aprés Sport: that time when a sportsman’s endeavors end and social life begins. 

Inspired by some of the world’s finest ball sports – the type of games prevalent on Ivy League campuses in the 50s – expect high-quality hoodies, sweats, and tees in an athletic yet forgiving fit—the definition of athleisure.

8. Jack Wills

Jack Wills was founded by Peter Williams and Robert Shaw in 1999. The brand’s original store opened at 22 Fore Street, Salcombe, and was created to bottle what being at a British university was all about. Today, Jack Wills combines heritage style with:

• A youthful

• Irreverent

• Carefree edge
  
  

The label quickly went mainstream in the 2000s and was viewed as the UK’s answer to Abercrombie & Fitch.

9. Abercrombie & Fitch

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

A&F’s signature moose logo was once the badge to be seen in, but its pull has since waned. In recent years, the brand has changed tack and refocused on what helped make its name in the first place. High-quality preppy basics that epitomise that laid-back California lifestyle.

10. Tommy Hilfiger

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

11. GANT

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

• The perfect collar roll

• Locker loop

• Box pleat

• Back collar button

• Button tab
  
  

Located near Yale University, the US label significantly shaped the Ivy League Look as we know it today.

12. Hackett

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

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

13. Drake’s

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

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

14. G.H.Bass

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

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

15. Sperry

Sperry is the original American brand of boat shoes, first designed in 1935 by Paul A. Sperry. Rumor has it that while sailing on the Long Island Sound, Sperry slipped on the deck of his boat and fell overboard, an experience that drove him to develop a safer, non-slip shoe. 

Multipurpose, the Sperry Top-Sider Deck (or boat) shoe has been seen on various celebrities and presidents, including JFK.

16. Beams Plus

It’s an oft-repeated opinion in menswear circles that Japanese fashion didn’t just adopt preppy Americana—it perfected it. The classic Ivy League look of the 1960s was lifted wholesale by Japanese prepsters and brands alike, who then began crafting their versions of preppy fashion. Beams Plus is one of the most beloved and enduring labels to do this. 

Part of a huge retail empire that stretches back to the 70s, it combines heritage menswear and rugged workwear to create its take on so-called Ametora or Japanese Ivy. Think of well-made garments with generous cuts and nerdy details.

17. LL Bean

Founded in New England, the spiritual home of preppy fashion, LL Bean is one of the most historic and influential American brands. It is renowned for its hardy, well-made outdoor gear. It’s more rugged than some preppy labels, but the collection is also vast. 

Among the camping gear and workwear, you’ll find:

• Smarter chinos 

• Oxford shirts. 
  
  

The label offers many classics, starting with its:

• Chamois shirts

• Logo tees

• Quarter-zip tops
  
  

18. Lacoste

Preppy fashion has always been a combination of dapper menswear and classic sportswear. In that sense, Lacoste is one of the quintessential preppy brands; its famous crocodile-emblazoned polo shirt was the creation of French tennis maestro Rene Lacoste. He wore the shirt on the court and quickly realized it looked great off-court, too. The rest is history. 

The brand isn’t all about the polo, however. You’ll also find other preppy classics in its collections, from knitted V-necks and sweatshirts to zip-up track tops.

19. Crew Clothing

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

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

20. Noah

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

• Skatewear 

• Preppy fashion
  
  

Preppy Modernity

There’s a heavy dose of JFK-lite nautical style, plus slacks and loafers, but it’s mixed with:

• Big graphic tees

• Eye-popping prints
  
  

Somehow, it just works, and it’s easy to wear.

21. Ivy Ellis

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

22. Vineyard Vines

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

• Polos

• Ribbed sweaters
  Button-down shirts

• Slacks

• Shorts 

• Casual tailoring
  
  

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

23. Armor-Lux

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

• Sailing-style raincoats

• Polo shirts

• Blazers 

• Fisherman jumpers
  
  

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

24. Aime Leon Dore

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

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

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