Consider you're standing in front of your closet or contemplating your living room, yearning for that perfectly polished yet effortlessly modern look. You want sophistication, but with a twist—enter Preppy Aesthetic. It's not just about the classics like crisp button-ups or monogrammed pillows; it’s about adding fresh, playful updates that keep you on trend. This guide will show you how to seamlessly blend timeless elegance with a modern vibe across your wardrobe and home decor.

To make this journey even smoother, there’s an app that can help: WhatColors’ AI personal color analysis. This tool lets you pick the right shades to create that chic, cohesive Aesthetic Preppy style in every aspect of your life.

Table of Contents

• What is the Aesthetic Preppy Look?

• 9 Key Elements of the Preppy Aesthetic Wardrobe

• How the Preppy Aesthetic Has Evolved Over Time

• Popular Colors and Patterns in Aesthetic Preppy Fashion

• Hottest Preppy Aesthetic Trends for 2024

• Can You Create a Preppy Aesthetic Room?

• Top 12 Preppy Aesthetic Accessories to Boost Your Look

• Iconic & Fabulous Preppy Aesthetic Celebrities

• 42 Preppy Aesthetic Ideas for Casual Occasions

• Try AI Personal Color Analysis For Free Today
  
  

What is the Aesthetic Preppy Look?

The Roots of the Preppy Aesthetic

The preppy aesthetic traces its origins to the early 1900s, emerging from the leisure activities of the upper class, including polo, sailing, and rugby—this connection to sports led to clothing styles with equestrian details, nautical stripes, and tailored suits. As Brooks Brothers became the go-to brand for students at Harvard, Yale, and Princeton, Ivy League schools became the epicenter of this fashion movement. Initially, this style was a form of collegiate rebellion but eventually became a staple of Ivy League culture. By the 1930s, the trend expanded to include women, and with the introduction of “Lady Levis” in 1934, the aesthetic was firmly established.

The Evolution of Preppy Style

The 1950s saw a resurgence of the preppy style, incorporating more denim and a sexier, tighter fit. The 1980s brought further evolution with the release of The Official Preppy Handbook and style icons like Brooke Shields and Princess Diana. By the late '90s, brands like J.Crew made preppy fashion more accessible, while pop culture figures like Britney Spears added a provocative twist. The 2010s saw a decline in the popularity of aesthetics, which was overshadowed by the rise of athleisure. But prep is returning, adapting to modern sensibilities while retaining its timeless charm.

Modern Preppy Subgenres

Today's preppy aesthetic is more diverse and inclusive, with distinct subgenres influenced by geography. Southern prep is bright, colorful, and whimsical, reminiscent of 1980s Yuppie culture rather than traditional Ivy League roots. Northeastern prep is more academic and collegiate, with a preference for plaid, navy, cream, and tweed. This style is upscale and British-influenced, emphasizing social achievement and class distinction. Americana prep is distinctly American, featuring Ralph Lauren-inspired looks, jeans, and patriotic elements like the American flag.

The Enduring Appeal of Preppy Style

Preppy fashion remains popular because of its timelessness, versatility, and adaptability. Classic preppy pieces like Oxford shirts, chinos, and blazers are essential elements of a well-rounded wardrobe, and they can easily transition between casual and dressy settings. The style also incorporates modern trends and influences, allowing individuals to personalize their looks while staying true to preppy roots.

What Preppy Looks Like in 2024

In 2024, the preppy aesthetic continues evolving, embracing brighter colors, inclusivity, and a casual vibe. Generation Alpha reinterprets preppy silhouettes with contemporary brands like Loveshackfancy and Lululemon. They experiment with bold colors and patterns, mixing preppy elements with other trends to express their individuality. The modern preppy aesthetic blurs the lines between formal and casual, with relaxed items like denim jackets and sneakers paired with traditional preppy pieces.

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9 Key Elements of the Preppy Aesthetic Wardrobe

1. Pleated Skirts: A Preppy Staple

The pleated skirt is a linchpin in the preppy wardrobe. Think plaid or muted grays that echo the classic private school uniform. As temperatures drop, pair these with monogram tights or knee-high socks. Not into pleats? A simple khaki version works just as well.

2. Button-Downs: The Versatile Classic

A crisp button-down is indispensable. Whether you prefer a slim fit or oversized, this piece offers unmatched versatility. Pair it with skirts or trousers for a polished, quintessentially preppy look.

3. Mary Janes: The Revamped Classic

Mary Janes has graduated from schoolgirl staple to fashion-forward footwear. The classic rounded toe and strap now come in updated, trendy versions. Wear them to add a touch of nostalgia to your ensemble.

4. Varsity Sweaters & Jackets: Sporty and Chic

Varsity jackets and collegiate sweaters are your go-to sporty pieces. Opt for dark hues like burgundy or navy to add a cozy element to your fall wardrobe. These pieces lend a touch of athleticism while keeping the overall look polished.

5. Blazers: Boost Your Ensemble

A great blazer can boost any outfit. If you like the oversized trend, pair it with a cute necktie or a school crest detail. This versatile piece adds a layer of sophistication to your preppy style.

6. Khakis & Trousers: The Pant Alternative

Khakis and trousers are essential for those who prefer pants. These sturdy options offer a classic look that complements pleated skirts while providing comfort and ease.

7. Loafers: The Chunky Upgrade

Loafers are having a moment, especially with chunky silhouettes. These shoes add an edge to your preppy style, making them a must-have in your fall shoe rotation.

8. Classic Jewelry & Statement Socks: The Finishing Touches

Accessories complete any outfit. For a preppy aesthetic, opt for plush knee-high socks and simple yet elegant jewelry. Think of gold hoops, pearl strands, and diamond tennis bracelets for a touch of elegance.

9. Patterns and Fabrics: The Preppy Palette

Preppy fashion relies on traditional patterns like plaid, stripes, and argyle. These add visual interest while maintaining a classic appearance. High-quality fabrics like cotton, wool, and cashmere are essential for comfort and style.

Embrace the Preppy Aesthetic: Perfect Colors for Your Style

Want to raise your style even more? Unlock your colors and transform your look with WhatColors’ AI personal color analysis app. Get your color analysis done in just 60 seconds. Download the app for free today on the App Store or Google Play store.

How the Preppy Aesthetic Has Evolved Over Time

From Ivy League Roots to TikTok Trends

The preppy aesthetic has dramatically transformed from its Ivy League origins to today’s fashion landscape. In the late 1890s and early 1900s, the preppy style was all about minimalism and elegance, serving as a status symbol for wealthy students at preparatory and Ivy League schools. Brooks Brothers button-downs, knit sweaters, and loafers were the staples of this look. By the 1930s, college women embraced the style, adding jeans to the mix after the release of "Lady Levi's" in 1934.

Fast forward to today, and the modern preppy aesthetic is a colorful, casual blend of bold patterns and athleisure-inspired pieces. Social media platforms like TikTok have played a significant role in redefining the preppy aesthetic for Gen Z. New versions of preppy style have emerged, including "VSCO preppy" and ironic preppy styles. The modern preppy look is less about crisp, pastel polos and pleated skirts and more about relaxed, beachy Southern charm.

The Evolution of Preppy Style

The evolution of the preppy style can be traced through specific decades. In the 1950s, the trend expanded to include sporty rugby shirts, plaid patterns, and Americana influences like bowling shirts and denim. By the 1980s, preppy style had become more mainstream, thanks to the influence of brands like Tommy Hilfiger, Calvin Klein, and Lacoste. The 1990s brought a new twist to preppy style with lower pants styles, boot cuts, and a sexy schoolgirl look popularized by Britney Spears.

In the 2000s, Jenna Lyons shook up the preppy style as J.Crew's creative director, introducing shockingly bright colors, sparkle, and playful twists. By 2015, the rise of athleisure made joggers and leggings more appealing than button-ups. The preppy style has undergone another metamorphosis today, with fashion week collections featuring mid-length skirt suits, collegiate sweaters, and plaid patterns.

The New Preppy Aesthetic: Confusing or Exciting?

The new preppy aesthetic has confused some people, especially those who grew up with the old preppy style of the late '90s and early 2000s. For them, preppy means crisp, pastel polos, pleated skirts, and cable-knit sweaters around the shoulders. The new preppy look, however, is more challenging to define, with a more relaxed, beachy Southern charm. While some people find the new preppy exciting and modern, others prefer the old style for its clean, professional look.

Despite the confusion, the new preppy aesthetic is catching on and will likely stick around for a while. Whether you prefer the old or new preppy style, there's no denying that the aesthetic will continue to evolve, reflecting each generation's changing tastes and preferences.

Popular Colors and Patterns in Aesthetic Preppy Fashion

Signature Preppy Colors

The preppy style embraces a color palette that’s both classic and fresh. Think navy blues, whites, khakis, and pastel hues. These colors form the backbone of the aesthetic, creating a timeless and elegant look. For preppy men, dark blue is a standout choice. It’s reserved and tasteful and pairs seamlessly with beige, white, or even light gray and blue. 

Lighter shades like beige and camel offer a modern touch. A hint of dark red or green adds interest without overwhelming the look. Avoid too many dark browns—they can quickly feel outdated in this context.

Patterns That Define Preppy

Patterns are critical to preppy fashion, providing structure and elegance. Plaid, checks, stripes, and tweed lead the way, often seen in tailored blazers, chinos, and skirts. For a playful twist, polka dots and leopard print accessories like scarves and handbags do the trick. Gingham checks bring a sense of freshness and youthful energy to sundresses and button-downs, especially in the warmer months. These patterns add dimension to the preppy aesthetic, keeping it lively without being overly bold.

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Hottest Preppy Aesthetic Trends for 2024

Laid-Back Preppy Trends for Men

Modern Preppy Style: Remixing Tradition

Men’s preppy style has evolved from the prim-and-proper Ivy League look to something more relaxed and expressive. Instead of sticking to blazers and tweeds, men are adopting a high/low dressing approach. Think denim jackets with tailored trousers or varsity jackets paired with roll necks. It’s about combining traditional preppy elements with casual pieces to create a fresh, modern aesthetic. This relaxed approach lets you nod to heritage while exploring the endless possibilities of menswear today.

Embracing Texture and Color

Texture and color are essential in today’s preppy style. The mix includes Corduroy trousers, madras check shirts, and striped rugby shirts. The idea is to incorporate these textures unexpectedly, like combining a navy blazer with textured wool trousers. Meanwhile, color-blocked ski jackets and bold striped polos infuse outfits with vibrant energy. This is not about blending in but standing out while still grounded in the preppy tradition.

Sportswear Influence

The influence of sportswear on preppy style is undeniable. Sweatpants and hoodies are being mixed with more traditional pieces, like tailored trousers and loafers. This creates a youthful, sporty vibe that is perfect for a relaxed weekend look. It’s about finding that balance between comfort and style, and today’s preppy aesthetic allows for a lot of play.

Women’s Preppy Trends: Sexy and Defiant

Breaking the Rules

Women’s preppy style in 2024 is all about breaking the rules. Forget the prim, buttoned-up looks of the past. Today’s preppy aesthetic is sexy, defiant, and full of personality. It’s about wearing a miniskirt so short the pockets hang out or a button-down shirt with no bra. This new take on preppy style is about expressing yourself and your discontent with our current systems. It’s about showing the world you’re not afraid to break the rules and be naughty.

Borrowing from the Boys

For so long, preppy style was all about the boys. Women had to borrow from men’s wardrobes to get in on the fun. But today, preppy style is for everyone. Women are taking traditional men’s pieces—like rugby shirts and blazers—and making them their own. It’s about taking these classic pieces and giving them a sexy, feminine twist. It’s about wearing a rugby shirt with nothing but a bra and a low-rise pleated skirt.

Embracing Color and Pattern

Color and pattern are key to today’s preppy aesthetic. From bold, bright colors to wild patterns, today’s preppy style is anything but boring. It’s about taking these traditional elements and pushing them to the extreme. It’s about wearing a Madras check shirt with leather pants or a bright yellow rugby shirt with a skirt so short it’s practically a belt. This is not about blending in; it’s about standing out and making a statement.

Can You Create a Preppy Aesthetic Room?

The Preppy Room: A Classic Look

Consider your living space echoing the elegance of a preppy wardrobe. Picture crisp lines, timeless materials, and a splash of playful patterns. This aesthetic draws inspiration from the classic style of New England prep schoolers and Ivy Leaguers, dating back to the late 1890s and early 1900s. 

The 1980s brought us Lisa Birnbach's "The Official Preppy Handbook," cementing this look into a cultural style staple. It's been around for ages, but the preppy look is still strong. People of all ages sport it in various forms today. The style is so timeless that it never really goes out of style. If you're curious about bringing this look into your home, check out these preppy room ideas.

Embrace Pink

Pink isn’t just for kids’ rooms—it’s a staple in preppy decor. This cheerful color can be used in any space, from the kitchen to the living room. It can make a strong statement in a guest room, especially with small details like tassels on nightstand drawer pulls.

Cane Furniture

Cane furniture is a must-have in preppy spaces. Pair pieces like a console or chair with bright colors to keep things looking fresh and fun. Burlwood is another preppy favorite, often seen in mirrors and other accents.

Pink and Blue

While pink and green are a classic preppy color combo, don’t be afraid to mix them with pink and blue. Sweet shapes and patterns, like scalloped edges and stripes, are vital to nailing this look.

Coastal Accents

Preppy spaces often lean coastal, so feel free to incorporate seaside elements like wicker, soft white fabrics and lots of blue tones.

Navy

Navy is another favorite preppy hue that complements a variety of other colors. A layered, scalloped mirror can add a touch of elegance to a bathroom.

Orderly and Sophisticated

Preppy spaces are known for their orderly and sophisticated vibe. Touches like a stylish table lamp, framed photos, and a vase filled with fresh flowers can go a long way in achieving this look.

Animal Motifs

Preppy rooms can be playful, so don’t be afraid to bring in some animal motifs. For example, a charming wicker elephant stool can add a sense of whimsy to a space.

Gingham

Gingham is a classic preppy pattern that can be used on everything from tablecloths to curtains. In a child’s room, blue-and-white gingham wallpaper is a great way to add some fun and color.

Jute Rug

Jute rugs are durable, classic, and often found in preppy spaces. Preps tend to invest in well-made pieces that stand the test of time, and a jute rug is a perfect example.

Wicker

Budget-friendly wicker is another must-have in preppy homes. A whimsical bookcase, for example, can add texture to a pastel pink room.

Famous Patterns

Some patterns, like Scalamandré zebra print, are immediately associated with preppy style. It's used in blue and white and’s perfect for a child’s room.

Bistro Chairs

French bistro chairs, available in various festive colors, are standard in preppy dining spaces. Preps love to host and gather with friends, so a dining room that can accommodate the whole crew is necessary.

Equestrian Decor

Many preppy rooms feature an equestrian-themed design, often in the form of wall art. For example, a picture depicting a horse race can pop against a backdrop of white, beige, and navy wallpaper.

Paisley

Paisley is a preppy print that’s been around for quite some time and doesn’t appear to be going anywhere. Preps are all about embracing tried-and-true decorating styles rather than experimenting with trends.

Ikat

Ikat is a beautiful print that’s making a comeback. In a dining nook, it can be the perfect spot for sipping coffee and getting some work done.

Stripes

Preps will always have a soft spot for stripes. Striped furniture and decor, such as sofas, pillows, rugs, and wall coverings, are more than suitable for a preppy room.

Outdoor Influences

Preps love gardening and spending time outdoors. Green-and-white botanical print wallpaper, for example, can bring the outdoors inside to a breakfast room.

Bathroom Upgrade

Even your powder room can get a preppy upgrade. Swap out builder-grade sconces for scalloped alternatives, jazz up your drawer pulls with tassels, and use a metal julep cup to hold toothbrushes.

Childlike Wonder

Kids’ rooms are perfect for experimenting with stripes and loud patterns. A green-and-pink canopy, for example, can transform a standard daybed into a dreamy spot to unwind.

Trunks

Preppies love their trunks. These fabulous storage solutions can be placed in any space and can even double as a nightstand if you're short on space.

Pink Shower

Make everyday tasks more fun by installing pink-and-white-striped tiles in your shower for a slightly eccentric take on preppy style.

Tropical Vibes

A pink-and-green color combo is perfect for a beachside property. Preps are all about celebrating and having fun, so don’t shy away from bright colors.

Thoughtful Pieces

Wicker parasol lamps are standard in preppy spaces and serve as works of art. Preppy homes are full of personality without being cluttered, so each furniture item and accent piece should genuinely serve a purpose.

Classic Palette

An understated preppy sunroom with a classic palette of blues, whites, and grays is bound to stand the test of time.

Florals and Stripes

Pairing stripes and florals is a classic preppy look. Hydrangeas can be a suitable flower choice for a lounge or home office.

Sports Gear

Ivy League banners and sports gear can help create a preppy vibe in a boys' room. A bold white, red, and green palette with traditional furnishings and decor will reinforce the look.

Indoor Putting Green

What could be more preppy than an indoor putting green? It’s the perfect way for the golf fanatic to bring some of the course indoors.

Top 12 Preppy Aesthetic Accessories to Boost Your Look

1. Hair Bows: A Timeless Preppy Essential

Hair bows are a long-standing staple in the preppy aesthetic. These chic accessories can be styled in various ways. Whether you prefer a single large bow or a collection of smaller ones, they effortlessly add a touch of elegance to your look.

2. Headbands: Your Go-To Preppy Accessory

Headbands are a classic preppy accessory that can save the day on a bad hair day. From simple to embellished, there’s a headband for every occasion. Look for ones with a loose bow for that iconic Blair Waldorf vibe.

3. Hair Scrunchies: Preppy Hair Made Easy

Scrunchies are a versatile accessory for achieving preppy hairstyles. They come in various colors and prints, allowing you to personalize your look. Use them to create sleek buns or pull your hair up for a polished appearance.

4. Neck Scarves: A Preppy Staple

A neck scarf is a quintessential preppy accessory. These small pieces of fabric add color and print to your outfit while keeping it polished and elegant. Opt for softer fabrics like silk for the ultimate preppy vibes.

5. Tights: The Preppy Layering Essential

Tights are a must-have accessory for the preppy aesthetic, especially in cold weather. Black tights boost your look and keep you warm when worn under shorts, skirts, or dresses. For a pop of color, consider statement shades like yellow or red.

6. Pins and Brooches: Vintage Meets Modern Preppy

Pins and brooches are making a comeback as chic accessories. These pieces personalize your look; you can easily find vintage or unique brooches in thrift stores. Clip them onto jackets or dresses for extra glam.

7. D-Ring Belts: Preppy Casual Refinement

A classic preppy D-ring belt in leather or ribbon is a versatile accessory. Look for belts in preppy motifs like stripes, embroidered critters, or solid colors to add a touch of refinement to any outfit.

8. Baseball Caps: Casual Preppy Vibes

A well-worn baseball cap is a preppy staple for casual outings. Choose caps with small logos or none, and opt for traditional colors like navy, red, or green. They’re perfect for bad hair days, too.

9. Rope Bracelets: Nautical Preppy Charm

Nautical-inspired rope bracelets add a playful touch to preppy outfits. Stack them with your watch or wear them independently for a laid-back, nautical vibe. They’re a great way to incorporate color and texture into your look.

10. Timepieces: Classic Preppy Elegance

A classic, understated wristwatch is a must-have accessory for any preppy dresser. Look for simple, elegant designs from high-end brands like Rolex or Omega. A leather or NATO strap adds a touch of casual sophistication.

11. Neckties: Timeless Preppy Patterns

Invest in high-quality neckties in timeless patterns like repp stripes, polka dots, and paisley. Choose ties made from luxurious materials like silk or wool, and opt for widths that complement your jacket lapels and body type.

12. Pocket Squares: A Preppy Outfit Finishing Touch

A crisp white linen pocket square instantly raises any preppy outfit. Experiment with different folding techniques to add visual interest to your blazer or sport coat.

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Iconic & Fabulous Preppy Aesthetic Celebrities

Timeless Preppy Icons: Lilly Pulitzer, Jackie Kennedy, and Kate Middleton

Lilly Pulitzer’s signature shift dresses epitomize the vibrant preppy aesthetic, perfect for leisurely summer days. Jackie Kennedy’s refined elegance, with pearls, Ray-Bans, and flawless wardrobe choices, set a high bar for preppy fashion. Kate Middleton channels Jackie’s classic style, always looking impeccably put together in everything from designer gowns to casual daywear. They embody the enduring appeal of preppy fashion.

Preppy Pop Culture Icons: Blair Waldorf and Nancy Drew

Blair Waldorf from Gossip Girl represents the ultimate preppy style queen with her love for color, structured silhouettes, and designer fashion. Her wardrobe is a dream for any prepster, filled with timeless pieces that are always prim and proper. Nancy Drew, the fictional detective, is another pop culture icon whose style is quintessentially preppy. She epitomizes the classic prepster look with her buttoned-up cardigans, penny loafers, and can-do attitude. These characters continue to inspire today’s preppy fashion trends.

Classic Preppy Icons: Grace Kelly, Gwyneth Paltrow, and the Kennedys

Grace Kelly’s classic, feminine style remains a source of preppy inspiration with her chic, modest dresses and menswear-inspired looks. Gwyneth Paltrow has embraced preppy fashion, often wearing sweaters with button-downs, cardigans, and timeless dresses. The Kennedy family, notably John F. Kennedy, epitomized the preppy lifestyle with their effortless blend of casual sophistication and polished elegance. These icons continue to influence the preppy aesthetic today.

The Lasting Influence of Ralph Lauren and Brooks Brothers on Preppy Fashion

Ralph Lauren has played a pivotal role in defining contemporary preppy fashion with his rustic charm and East Coast elegance. His designs have broad appeal, transcending generations and geographies. Brooks Brothers, the oldest men’s clothier in the United States, has outfitted generations of Ivy Leaguers, Presidents, and professionals, cementing the Ivy League look as a cornerstone of men’s preppy style. These brands have left a lasting impact on the preppy aesthetic.

Modern Celebrities Reinventing Preppy Style: David Beckham and Ryan Reynolds

David Beckham and Ryan Reynolds exemplify how preppy style continues to evolve, blending traditional tailoring with modern influences. Beckham often mixes classic preppy pieces with sporty elements, while Reynolds opts for clean, polished ensembles with a touch of whimsy. These modern influencers showcase preppy fashion's versatility and enduring appeal, adapting the look to suit their style.

42 Preppy Aesthetic Ideas for Casual Occasions

1. Classic Chino & Polo Combo

Embrace timeless elegance with well-fitted chinos and a crisp polo shirt. For versatility, opt for neutral colors like beige or navy. Complete the look with loafers or clean white sneakers. This outfit is ideal for casual Fridays or weekend brunches, combining comfort with a touch of style.

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A crisp polo shirt in neutral colors like beige or navy.

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Well-fitted chinos for a versatile and polished look.

2. Nautical-Inspired Layers

Channel maritime vibes with a striped boatneck sweater layered over a collared shirt. Pair with tailored shorts or chinos and boat shoes for a laid-back, yet polished look. This style is perfect for coastal getaways or summer weekends, blending functionality with preppy charm.

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A striped boatneck sweater layered over a collared shirt.

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Tailored shorts or chinos to enhance the nautical vibe.

3. Smart Casual Blazer & Jeans

Boost your casual look by pairing a lightweight blazer with dark-wash jeans and a well-fitted button-down shirt. Choose loafers or brogues to complete the ensemble. This outfit balances relaxed and refined, making it suitable for semi-formal events or smart-casual outings.

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A lightweight blazer over a button-down shirt.

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Dark-wash jeans that balance casual with nuance style.

4. Preppy Vest Ensemble

Layer a sleek vest over a collared shirt for a polished yet relaxed appearance. Combine with chinos or tailored jeans and loafers. This look is great for transitional seasons and adds more sophistication without being overly formal.

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A sleek vest layered over a collared shirt.

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Chinos or tailored jeans for a polished yet relaxed feel.

5. Textured Sweater & Trousers

Choose a cable-knit or patterned sweater and pair it with slim-fit trousers. Opt for loafers or casual boots to round off the outfit. This combination is perfect for cooler weather and offers a refined yet comfortable look, ideal for casual gatherings or day trips.

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A textured sweater such as a cable-knit or pattern.

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Slim-fit trousers that offer a refined and sleek outline.

6. Varsity Jacket Style

Embrace collegiate flair with a classic varsity jacket over a simple tee or henley shirt. Combine with jeans or chinos and sneakers for a youthful, sporty vibe. This outfit is perfect for a casual day out or social events where a touch of nostalgia adds to the fun.

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A classic varsity jacket over a simple tee or henley.

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Jeans or chinos that complement the youthful, sporty vibe.

7. Preppy Knit Polo & Shorts

Choose a knit polo shirt and pair it with tailored shorts for a polished summer look. Finish with loafers or boat shoes for an effortlessly sophisticated outfit. This style is ideal for warm weather activities, offering comfort and elegance.

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A knit polo shirt for a refined summer aesthetic.

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Tailored shorts for a clean, preppy look.

8. Sophisticated Henley & Denim

Opt for a well-fitted henley shirt paired with dark denim jeans. Add loafers or desert boots for a touch of sophistication. This outfit strikes a great balance between casual and refined, making it suitable for both relaxed and semi-formal occasions.

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A fitted henley shirt for a casual yet polished upper layer.

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Dark denim jeans to keep the look sharp and sleek.

9. Checks & Chinos

A classic checkered shirt paired with chinos creates a preppy, yet casual look. Roll up the sleeves for a more relaxed vibe and add loafers or sneakers. This outfit is perfect for a casual day at the office or a weekend outing.

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A classic checkered shirt, rolled up for a more relaxed feel.

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Chinos to maintain the preppy yet casual look.

10. Layered Cardigan & Oxford Shirt

A button-down oxford shirt layered with a fitted cardigan offers a refined, comfortable style. To complete the look, combine with chinos or jeans and loafers. This outfit is ideal for cooler weather, providing both warmth and sophistication.

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A fitted cardigan over a button-down oxford shirt.

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Chinos or jeans for a versatile, smart-casual look.

11. Striped Shirt & Blazer

Combine a striped dress shirt with a casual blazer for a smart, preppy look. Pair with tailored trousers or chinos and polished loafers. This ensemble is perfect for occasions where a touch of formality is required but you still want to maintain a relaxed feel.

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A striped dress shirt under a casual blazer.

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Tailored trousers or chinos for a refined finish.

12. Crewneck Sweater & Slim Jeans

A classic crewneck sweater over a collared shirt paired with slim-fit jeans offers a relaxed yet polished look. Opt for loafers or casual boots to complete the outfit. This style is ideal for cooler days and provides a comfortable yet stylish option.

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A classic crewneck sweater over a collared shirt.

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Slim-fit jeans for a relaxed yet polished look.

13. Preppy Parka & Khakis

A sleek parka over a button-down shirt paired with khakis creates a polished, preppy look perfect for colder weather. Casual boots or loafers complete the outfit. This combination balances style with practicality, ideal for both urban and rural settings.

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A sleek parka layered over a button-down shirt.

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Khakis for a casual yet stylish outfit perfect for colder days.

14. Polished Tee & Tailored Shorts

Opt for a high-quality, fitted tee paired with tailored shorts for a casual yet refined summer look. Finish with boat shoes or loafers. This outfit is great for beach days or casual outings, offering comfort with a touch of sophistication.

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A high-quality, fitted tee for a casual yet elegant top.

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Tailored shorts for a preppy and laid-back summer vibe.

15. Elegant Button-Down & Sweater Vest

Layer a button-down shirt with a sweater vest for a preppy and refined look. Combine with chinos or dress trousers and loafers. This ensemble is ideal for semi-formal occasions or cooler days when you want to maintain a polished appearance.

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A button-down shirt paired with a sweater vest for a polished appearance.

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Chinos or dress trousers for a sophisticated finish.

16. Casual Suit & Sneakers

A lightweight, casual suit paired with clean sneakers creates a modern, preppy look. For versatility, opt for a relaxed fit and neutral colors. This outfit is perfect for events where you want to combine comfort with style, like casual business meetings or social gatherings.

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A lightweight, casual suit jacket for a raised look.

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Relaxed-fit trousers and sneakers for a modern preppy style.

17. Classic Trench & Slim Trousers

A well-tailored trench coat over a collared shirt and slim trousers offers a sophisticated, preppy look. For a polished finish, complete with loafers or boots. This ensemble is perfect for transitional weather and provides an elegant yet practical option.

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A well-tailored trench coat layered over a collared shirt.

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Slim trousers for a sleek and elegant silhouette.

18. Preppy Jumper & Denim

Choose a classic jumper over a collared shirt, paired with dark denim jeans. Opt for loafers or casual boots to complete the look. This outfit is perfect for cooler days and combines comfort with a refined touch.

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A classic jumper layered over a collared shirt.

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Dark denim jeans for a refined yet relaxed outfit.

19. Casual Blazer & Casual Tee

A casual blazer worn over a simple tee and paired with chinos or jeans offers a modern, preppy look. Finish with loafers or clean sneakers. This outfit is ideal for relaxed social events or casual business settings, providing a blend of sophistication and ease.

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A casual blazer over a simple tee for a smart-casual look.

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Chinos or jeans for a relaxed but stylish combination.

20. Button-Down & Corduroys

A well-fitted button-down shirt paired with corduroy trousers creates a stylish, preppy look.
Add loafers or casual boots to complete the outfit. This combination is perfect for fall or winter days, offering both comfort and elegance.

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A well-fitted button-down shirt to create a preppy top layer.

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Corduroy trousers for texture and a touch of fall or winter style.

21. Preppy Pullover & Dress Pants

A classic pullover sweater over a collared shirt paired with dress pants offers a refined, preppy look. Finish with loafers or oxford shoes. This outfit is ideal for smart-casual events or cooler days when you want to maintain a polished appearance.

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A pullover sweater layered over a collared shirt.

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Dress pants for a more formal, preppy appearance.

22. Elegant Overcoat & Casual Jeans

Layer an elegant overcoat over a collared shirt and casual jeans for a sophisticated, preppy look. Opt for loafers or dress boots to complete the outfit. This ensemble is perfect for cooler weather and provides a stylish, polished option.

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An elegant overcoat over a shirt for a sophisticated outer layer.

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Casual jeans for a laid-back but stylish contrast.

23. Preppy Vest & Chinos

A sleek vest worn over a collared shirt, paired with chinos, offers a stylish yet casual look. Finish with loafers or casual shoes. This outfit is ideal for transitional seasons and adds a touch of sophistication to everyday wear.

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A sleek vest layered over a collared shirt.

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Chinos for a polished yet casual bottom half.

24. Modern Varsity & Slim Jeans

A contemporary varsity jacket paired with slim jeans and a simple tee creates a stylish, preppy look. To complete the outfit, opt for sneakers or loafers. This style is perfect for a youthful, casual vibe with a touch of nostalgia.

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A modern varsity jacket over a simple tee.

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Slim jeans for a youthful, fitted look.

25. Casual Blazer & Linen Shirt

Pair a casual blazer with a linen shirt and tailored shorts or chinos for a relaxed yet sophisticated look. Finish with loafers or boat shoes. This outfit is ideal for warmer weather and offers a comfortable yet elegant option.

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A casual blazer paired with a breezy linen shirt.

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Tailored shorts or chinos for a relaxed yet elegant feel.

26. Preppy Pullover & Denim Shorts

A classic pullover sweater over a collared shirt, paired with denim shorts, creates a laid-back, preppy look. Add loafers or casual sneakers to complete the outfit. This style is perfect for casual summer days, blending comfort with a touch of sophistication.

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A pullover sweater layered over a collared shirt.

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Denim shorts for a casual yet preppy summer look.

27. Smart Casual Cardigan & Chinos

Layer a fitted cardigan over a collared shirt and pair with chinos for a smart casual look. Complete with loafers or casual boots. This outfit is great for cooler weather and offers a refined yet comfortable option.

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A fitted cardigan is worn over a button-down shirt.

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 Chinos for a classic smart-casual combination.

28. Tailored Sweater & Dress Jeans

Opt for a tailored sweater over a collared shirt paired with dress jeans for a polished, preppy look. Finish with loafers or casual boots. This ensemble is perfect for semi-formal events or smart casual outings, combining style with ease.

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A tailored sweater for a polished upper layer.

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Dress jeans for a refined yet relaxed bottom half.

29. Preppy Polo & Tailored Trousers

A fitted polo shirt paired with tailored trousers offers a sophisticated, preppy look. Add loafers or clean sneakers to complete the outfit. This style is ideal for both casual and smart-casual occasions, providing comfort and elegance.

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A fitted polo shirt for a classic preppy top.

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Tailored trousers for a sophisticated look.

30. Elegant Henley & Casual Trousers

Choose a refined henley shirt paired with casual trousers for a relaxed yet polished look. Finish with loafers or casual boots. This outfit is great for casual days and offers a comfortable, stylish alternative to traditional preppy wear.

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A refined henley shirt for a relaxed yet polished appearance.

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Casual trousers to complement the relaxed vibe.

31. Layered Hoodie & Slim Jeans

A sleek hoodie layered over a collared shirt paired with slim jeans creates a modern, preppy style. Clean sneakers or loafers complete the look. This outfit is perfect for a youthful, casual vibe with a touch of sophistication.

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A sleek hoodie layered over a collared shirt for contrast.

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Slim jeans for a modern, fitted look.

32. Preppy Blazer & Printed Shirt

Combine a classic blazer with a printed shirt and chinos for a stylish, preppy look. Add loafers or casual shoes to complete the outfit. This ensemble is ideal for social events or casual business settings, offering a blend of refinement and modern flair.

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A classic blazer layered over a printed shirt for a contemporary touch.

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Chinos for a sleek and preppy finish.

33. Casual Overcoat & Polo Shirt

Layer a casual overcoat over a polo shirt, paired with chinos or jeans, for a polished yet relaxed appearance. Finish with loafers or casual boots. This outfit is great for cooler weather, combining warmth with a sophisticated, preppy touch.

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A casual overcoat layered over a polo shirt.

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Chinos or jeans for a versatile and refined look.

34. Preppy Puffer & Casual Trousers

A sleek puffer jacket over a collared shirt paired with casual trousers creates a stylish, preppy look. To complete the outfit, opt for casual boots or loafers. This ensemble is perfect for colder days, offering both warmth and elegance.

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A sleek puffer jacket for a casual yet polished look.

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Casual trousers for a comfortable but stylish bottom half.

35. Smart Sweater & Tailored Shorts

A classic sweater over a collared shirt and tailored shorts offers a refined, preppy summer look. Finish with loafers or boat shoes. This style is ideal for warm weather outings, combining sophistication with comfort.

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A classic sweater worn over a collared shirt for a refined appearance.

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Tailored shorts for a preppy summer vibe.

36. Sweater Vests Are Your New BFF

Sweater vests have been big news recently, and we’re obsessed. This little piece of knitwear is the perfect finishing touch for a ’90s preppy outfit. Try wearing a checked sweater vest over a polo top or shirt and teaming it with tailored trousers for a cute preppy outfit. You can also tone down this outfit idea by ditching the prints and opting for plain neutral tones—which is great if you’re a fan of the vanilla girl trend.

37. Wear Your Jumper Over Your Shoulders

Sometimes, it isn’t what you wear, but how you wear it. Draping your knits over your shoulder is the perfect way to give even the simplest outfit a cute, preppy spin. The trick to getting this look right is to keep your whole outfit simple and make sure you’re draping your jumper over a casual t-shirt or polo neck top rather than over your bulky winter coat. Plus, if it suddenly gets cold or you want to cozy up, you’ve got an extra layer to hand.

38. Pair Socks With Your Mini

One combo we will always associate with the 90’s preppy aesthetic is the mini skirt and knee-high socks. This classic preppy outfit idea may seem a bit daunting and give you flashbacks of your school uniform, but trust us when we say it is more wearable than you’d think – you just need to keep it simple and wear it with confidence. And if getting your legs out feels a little too daunting, switch to a midi-length skirt teamed with a polo top and sunnies for a cool preppy summer outfit.

39. Switch to Your School Sweater

Prefer to keep it comfy in jeans & a hoodie? We’ve got you covered! Pairing an American-style slogan knit with your jeans will take your outfit from basic to a super cute daytime look. And it doesn’t stop with jeans, pairing a slogan sweater with a pleated skirt or over a summer dress is a super fun yet feminine way to wear the trend. Plus, this cute preppy outfit idea is an easy way to wear the matching couples trend – you just both need to wear the same school jumper!

40. Loaf-ing Around

If there is one shoe you should invest in to nail the preppy trend, it is the oh-so-versatile loafer. This shoe-drove classic will instantly give any outfit a preppy spin—even if that outfit is as simple as jeans and a chic shirt. Plus, let’s face it—they’re super comfortable and ideal for running around town for errands. What’s not to love?

41. Suit Up Your Hoodie

Give your tailored co-ord a street style-inspired update by wearing a hoodie underneath. Not only is this ensemble super comfortable, but it will make your suit feel more daytime appropriate – perfect if you’re going out for lunch or going on a coffee date.

42. Embrace the Bomber Jacket

Bomber jackets are set to be huge in 2023, so ditch your denim and biker jackets in favor of this retro style. The best bit about this new jacket trend is that you really have fun and play with colors. Try keeping it simple and wearing your bomber over sneakers, jeans, and a tee for an easy daytime look. Or try pairing a bomber over a mini skirt or dress and sneakers if you prefer to create more of a feminine, cute, preppy outfit.

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