As summer fades into cooler weather, many seek to refresh their wardrobes for autumn. Selecting new fall attire can be daunting. Will the purchase align with your personal style? Preppy photos offer a solution. These classic, cheerful images showcase fall outfit possibilities, building a versatile autumn wardrobe and elevating personal style. This blog shows how preppy photos contribute to achieving fall fashion goals.

WhatColors’ AI personal color analysis app can help you define your signature color palette and find preppy aesthetic photos that resonate with your unique style.

Table of Contents

• What Are Preppy Photos?

• How Preppy Got Cool Again – And How To Wear It Now

• 6 Iconic Preppy Photos Captured in 2024

• 7 Editing Tips for Achieving a Preppy Look

• Inspiration from Iconic Preppy Brands

• Top 15 Preppy Photo Ideas to Try

• Why Preppy Photos Are Trending

• Try AI Personal Color Analysis For Free Today

What Are Preppy Photos?

Preppy photos capture the essence of the:

• Preppy lifestyle

• Fashion aesthetic

They display the classic, clean-cut style associated with upper-class collegiate or country club culture.

Typical Elements in Preppy Photos

Clothing

Preppy photos typically feature outfits like:

• Polo shirts

• Oxford button-downs

• Khakis

• Boat shoes

• Blazers

• Pearls

Colors

Preppy photos emphasize pastel color palettes, navy, and earth tones, often with bold patterns like:

• Plaid 

• Stripes

Settings

Preppy photos are often set in environments like:

• College campuses

• Country clubs

• Beaches

• Upscale suburban areas

Activities

Preppy photos may depict leisurely activities such as:

• Sailing

• Golf

• Tennis

• Equestrian sports

Accessories

Preppy photos often include accessories like:

• Monogrammed bags

• Classic watches

• Statement jewelry

Atmosphere

Preppy photos convey a sense of:

• Affluence

• Tradition

• Polished casualness

Composition

Preppy photos usually present well-organized, clean, and bright images with attention to detail.

Lifestyle

Preppy photos reflect an idealized version of upper-middle-class American life, particularly associated with the Northeast.

Inspiration

For styling cues, preppy photos often draw from brands like:

• Ralph Lauren

• J.Crew

• Vineyard Vines

How Preppy Got Cool Again – And How To Wear It Now

The preppy style is back and better than ever, and its resurgence is fueled by nostalgia, social media, and a fresh new take on the classic look. The return of trends from the 1980s and 90s has been growing for a while, but TikTok and Instagram have made the modern preppy style more accessible.

Evolving Preppy Style

Platforms like TikTok are packed with Get Ready With Me videos that showcase how to style classic pieces in a contemporary way, making the look feel fresh and relevant. The new take on preppy style is eclectic and versatile, borrowing from other popular aesthetics like:

• Goth

• Grunge

• Y2K to create a look that feels universal

This blend has made the preppy style more appealing to Gen Z and younger millennials, who are less interested in setting trends and more focused on self-expression and individuality.

The Celeb Influence on Preppy Style

While the fashion industry is mainly responsible for bringing preppy style back into the spotlight, celebrities and influencers have also played a significant role in its revival. These style icons often mix classic preppy elements with contemporary streetwear or luxury fashion—creating a more attainable look and relatable to the masses. 

The Princess of Wales has been spotted wearing pieces from the preppy aesthetic for years. She was recently seen carrying a Longchamp Le Pliage bag on a royal tour, an item tied to preppy style. The accessory was made famous by college students in the Noughties, and its association with the royal family and the popular television show Succession has brought it back into the spotlight.

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6 Iconic Preppy Photos Captured in 2024

1. Taylor Swift's Preppy Plaid Blazer and Miniskirt

Taylor Swift stepped out in an olive, red, and magenta plaid blazer and miniskirt set from Vivienne Westwood. Under the three-quarter-sleeve blazer, she added a ruffly white blouse from the designer. 

The singer accessorized with ankle socks and olive Sézane Mary Jane pumps. Beauty-wise, she wore her hair down in loose waves and had on a red lip.

2. Zendaya's Suited Preppy Looks at Wimbledon

Zendaya was photographed in London attending Wimbledon this past weekend in not one, but two preppy, suited looks. On Sunday, she was photographed sitting courtside during the men's singles final wearing a Ralph Lauren Collection white linen day dress, a blue and white striped shirt, and a navy silk knit tie. 

Keeping in line with her preppy, menswear style, the Challengers star was spotted one day earlier at the women's singles final wearing:

• A Polo Ralph Lauren herringbone jacket

• Shirt

• Knitted tie

• Jeans

3. Blake Lively and Ryan Reynolds Match Preppy Vibes

Blake Lively has been incorporating flora and fauna into her street style and red-carpet looks as she promotes the movie, in which she plays a florist named Lily Bloom. (No, really.) She continued that thematic streak Thursday evening when she stepped out in a preppy look pulled straight from Thom Browne’s Fall 2024 couture runway show. 

Once again, the florals were the show's star, thanks to an embroidered boxy blazer that also happened to be covered in reflective rose gold sequins. As for Reynolds, the Deadpool star took his colorful, preppy approach. He wore a cream and lime green sweater vest casually layered over a white T-shirt with a streak of colors running through the center.

4. Gabrielle Union Looks Like a Preppy Sporty Spice

Some have stayed true to Team USA in red, white, and blue get-ups. Others are making their interpretations of the theme. Gabrielle Union has been scoring tens across the board for her athletic-meets-preppy ensembles. 

The actress attended the men's basketball final on August 8 in an outfit fit for a collegiate Sporty Spice. The outfit featured a boardroom on top and a tennis court on the bottom.

5. Billie Eilish's Casual Spin on Preppy Style

Billie Eilish put a casual spin on a preppy staple while performing at Sunday's 2028 Los Angeles Olympics handover celebration. Eilish, who performed alongside her brother and music producer Finneas, wore a Ralph Lauren polo shirt emblazoned with blue and red stripes and an American flag patch. 

The singer also wore khaki cargo shorts, accessorizing with:

• Nike sneakers

• Argyle socks

• A striped denim cap

6. Princess Kate Styles a Preppy Staple for a Surprise Olympics Video

On August 11, the Prince and Princess of Wales teamed up with:

• Snoop Dogg

• David Beckham and more to congratulate Team GB on their performance at the games

Royal Preppy Style

"From all of us watching at home, congratulations to team GB," Kate Middleton said in a rare appearance. The royals were dressed in coordinating blue, with William in an Adidas polo and Kate in a preppy staple–a Breton striped top from Ralph Lauren. 

Even the most cursory glance at Kate Middleton's outfit catalog clarifies that stripes are part of her style DNA.

7 Editing Tips for Achieving a Preppy Look

1. Bright is Right: Increase Brightness and Contrast for Preppy Aesthetic Photos

For clear, cheerful, preppy-style photos, start by increasing brightness and contrast. This will create a clean, fresh look characteristic of preppy style. 

Brighter images convey a sense of cheerfulness and optimism, while increased contrast defines:

• Clothing items

• Accessories

2. Cool it with the Tones: Emphasize Blues and Greens to Capture the Preppy Vibe

Cool tones are staples in preppy fashion. In your photos, emphasize blues (like navy) and greens (like mint or forest) to reinforce the preppy aesthetic. This can be done through selective color adjustments or split toning.

3. Up the Pastels: Boost Saturation of Pastel Colors for a Preppy Look

Pastels are quintessentially preppy. Increasing the saturation of colors like light pink, baby blue, or soft yellow will make these hues pop without looking unnatural.

4. Get the Details: Sharpen Textures and Patterns for Preppy Style Photos

Preppy style often features distinct textures (like cable knit sweaters) and patterns (such as argyle or plaid). Sharpen details on clothing textures and patterns to make them:

• More prominent

• Visually appealing

5. Selectively Enhance Key Colors Associated with Preppy Style

Focus on colors typically associated with preppy styles, such as:

• Navy

• Burgundy

• Forest green

• Khaki

Use selective color adjustments to enhance these hues and make them stand out more in your images.

6. Apply a Soft Vignette to Draw Attention to Preppy Outfits

A subtle vignette can help draw the viewer's eye to the center of the image, highlighting the preppy outfit or style elements. Keep it subtle to maintain a natural look.

7. Define the Layers: Enhance Shadows to Add Depth to Preppy Style Photos

Preppy style often involves layering (e.g., sweaters over collared shirts). Enhancing shadows can help:

• Define these layers

• Add depth to the overall look 

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Inspiration from Iconic Preppy Brands

J.Crew: The Go-To for Preppy Wardrobe Staples

All the preppy girls like to shop at J.Crew. It’s also one of our favorite preppy brands here at MCO for a good reason! This classic brand has a wide selection of timeless clothes. You can find everything from tweed dresses and button-down linen dresses to shirt dresses that are fit for:

• Tea parties

• Soirées

J.Crew also has no shortage of crisp white button-down shirts that embody a chic spirit. This famous preppy brand will also be your go-to shop for:

• Blazers

• Dress pants

• Cashmere sweaters

Tommy Hilfiger: Classic American Styles with a Modern Twist

Get ready to fall head over heels in love with the preppy pieces from Tommy Hilfiger. This legendary brand has been great at crafting iconic preppy college American styles since 1985. Tommy Hilfiger offers elevated and sophisticated pieces with a playful and modern twist. Tommy Hilfiger is calling your name if you want preppy clothes with a contemporary flair. 

You can find great American classics with a Tommy twist, like slim-fit polo shirts boasting the iconic TH logo. The brand also has polo dresses that would be great for rocking at country clubs. Other timeless and charming clothing items include:

• Relaxed straight-leg pants

• Oversized striped cardigans

• Khaki trench coats

• Leather mid-block heels

• Oxford shirts

Abercrombie & Fitch: The Perfect Preppy Uniform

Create the perfect preppy uniform with clothes from Abercrombie & Fitch. The brand's history dates back to 1892, when David Abercrombie, an outdoor specialty retailer, founded it. The company became Abercrombie & Fitch in 1904 when Ezra Fitch joined the brand. 

Abercrombie & Fitch Offerings

Since then, Abercrombie & Fitch has made clothes with an optimistic American spirit. If you’re looking for comfortable and classy dresses, Abercrombie & Fitch has:

• Premium linen midi dresses

• Poplin dresses

You will also love the:

• Tailored pants

• Polished polos

• Oversized poplin shirts

• Plenty and more elegant pieces

Tory Burch: Chic Handbags and Classy Ready-to-Wear

Adding pieces from Tory Buch will not be a decision you will regret. The brand was founded by American fashion designer Tory Burch in 2004. This New York-based brand is well-renowned for its irresistibly chic handbag collections. Some must-have handbags you need in your preppy closet are the following:

• Perry compartment tote bags 

• Robinson top handle bags

These timeless bags will look great with all your preppy outfits. In addition to the luxurious bags, Tory Burch has ready-to-wear pieces that are effortlessly polished. You will find everything from belted coats, poplin shirt dresses, collared crewnecks, smocked dresses, and tailored pants to many more incredible pieces.

Kate Spade: Feminine and Playful Preppy Styles

Kate Spade is an excellent place to explore for preppy and pretty clothing. The brand was founded by Kate and Andy Spade in 1993 to offer high-end bags at an affordable price point. Since its inception, Kate Spade has focused on providing pieces with an optimistic and feminine spirit. 

You will see floral crossbody bags, tote bags, and elegant clutches. Besides the fantastic bag collection, Kate Spade offers other cute and classy accessories. This includes:

• Floral print silk scarves

• Oval sunglasses

• Polka dot umbrellas

Kate Spade is also the place to look for polished and feminine clothing. You can find everything from stripe wrap dresses to floral one-shoulder dresses and spring gingham pants.

Lilly Pulitzer: For Timelessly Chic Preppy Clothes

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

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

Lilly Pulitzer Legacy

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

• Ruffle tops

• Relaxed button-down shirts

• Fun accessories

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

Vineyard Vines: Whimsical Prep for the Good Life

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

Vineyard Vines Aesthetic

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

• Straw tote bags

• Cashmere cardigans

• Silk shirt dresses

• More pieces that embody timeless elegance and coastal charm

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

Sperry: Preppy Boat Shoes for Nautical Style

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

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

• Styles

• Colors

• Finishes

Lacoste: The King of Preppy Polo Shirts

Have you ever wondered who was behind the idea of the shirts and clothes with the crocodile logo? Enter René Lacoste. The legendary Tennis champion René Lacoste invented the world’s first short-sleeved polo shirt in a breathable fabric to make playing tennis more comfortable. This shirt gave him a light-bulb moment to launch the brand Lacoste. He launched the brand with the principles of breaking fashion rules while keeping it classy and elegant.

Lacoste Brand Legacy

Inspired by his fearless skills on the court, Lacoste earned the playful nickname the crocodile. This nickname sparked the idea of making the crocodile his brand's logo. Now, the iconic crocodile is synonymous with:

• Effortless elegance

• Athletic chic style

Lacoste has all the elegant clothing items and must-haves to meet your preppy fashion needs. You will find everything from:

• Timeless sweater vests

• Monogram varsity jackets

• Polo shirts

• Tapered checkered pants

• Canvas tote bags

Talbots: The Classy Preppy Brand That Will Never Go Out of Style

Talbots is the type of preppy clothing brand you will never stop when you shop there. This women’s brand was founded in 1947 by Nancy and Rudy Talbot, emphasizing:

• Modern

• Classy

• Smile-worthy clothes for every occasion

Talbots is brimming with the best preppy clothes. From polished casual pieces like:

• Linen blazers

• Tweed collarless jackets

• V-neck sweaters

• Fabulous fancy dresses in its offering

Southern Tide: Coastal Prep with a Collegiate Spirit

Southern Tide is for the fashion-forward woman who loves a preppy and southern style. The brand was founded in 2006 in South Carolina. The first product to get them on the fashion map was their Skipjack polos. The polos became a hit in the fashion world because of their:

• Fit

• Design

• Comfort

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

Southern Tide Essentials

Think:

• Stripe dresses

• Wide-leg pants

• Twill shorts

• Crewneck t-shirts

What’s also great about Southern Tide is its unique collegiate collection so that you will have endless access to the best:

• Polo shirts

• Button-down shirts

Brooks Brothers: The Epitome of Preppy Style

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

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

• Linen dresses

• Polished polos

Rowing Blazers: The Newest Preppy Brand on the Block

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

• Bright colors 

• Unique touches

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

• Polo t-shirts

• Knits

• Leisurewear

Alice + Olivia: Whimsical Pieces for the Preppy Fashionista

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

Some bestseller items are:

• Denim dresses

• Wide-leg pants

• Midi dresses

You will be satisfied with their chic designs.

Land’s End: High-Quality Classy Basics for the Family

In 1963, Land’s End was founded on the principles of crafting high-quality clothing for the entire family. The brand combines elegance and functional designs to create timeless, comfortable pieces. Its aim is to make its clothes so soft and easy to wear that they feel like Sunday comfort every day. 

You will quickly put together the best preppy looks with the endless selection of:

• Blazers

• Coats

• Fleece tops

• Chino pants

Sporty & Rich: For the Ivy League Aesthetic

Want to look like a sporty and rich Ivy League student? You need to check out this timeless brand. It was established from a dreamy mood board about life’s beautiful moments, mixing past inspirations with modern elegance. The brand evolved from a chic print magazine to a preppy fashion brand that offers simple yet elegant styles that outlast the fashion calendar.

Wilfred: Feminine and Flattering Preppy Styles

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

Barbour: Timeless Outdoor Style

John Barbour established his namesake label in 1894. His most popular design for the brand is the wax cotton jacket, which was launched in 1936. Due to its style and durability, it became a go-to jacket for motorcycle riders. 

The luxury English brand has other great pieces that are exceptionally made and will stand the test of time. Barbour has a good collection of:

• Cardigans

• Jackets

• Tailored pants

• Boots

Hunter Boots: The Preppy Rain Boot of Choice

You’ve probably seen the royals and Hollywood celebrities sport Hunter Boots. This famous brand has amazing boots that will go with any preppy outfit you can think of. They can accompany jeans and a button-down blazer, a flowy wrap dress, or even a trench coat and jeans – the endless styling possibilities.

J.Mclaughlin: For Classic American Styles

Immerse yourself in the stylish and preppy world of J. McLaughlin. This brand was launched in 1977 by two brothers, Jay and Kevin, to craft classic American sportswear apparel with a modern twist. J. Mclaughlin prioritizes timeless style over fleeting trends. Plus, the J brand is all about designing clothes that are not pretentious. 

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

• Long sleeve tops

• Blazers

• Tailored shorts

• Polished accessories

Sail to Sable: Resort Wear for the Preppy and Classy

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

• Classic silhouettes

• Statement prints

• Dreamy summer adventures on the East Coast

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

Ted Baker: Preppy Styles with a British Flair

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

• Tote bags

• Romantic floral dresses

• Drape-neck tops

• Slingback pumps

Banana Republic: The Best Preppy Basics

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

• Blazers

• Trench coats

• Sweaters

• Wardrobe classics

Ralph Lauren

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

Price: $22 – $1,000

Michael Kors

Michael Kors is the epitome of chic and accessible luxury. American fashion designer Michael Kors started his namesake brand in 1981. For over 40 years, Michael Kors has always delivered the most fashionable pieces, which is why this brand should be your go-to for:

• Polished accessories

• Garments

Price range: $155 – 1,295

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Levi Strauss & Co.

Every preppy wardrobe needs a stylish, classy, and reliable pair of jeans. After all, jeans are the building blocks of most preppy outfits, so Levis is an excellent brand to check out. Levis, a brand that has shaped fashion and popular culture, was founded in 1853 by Levis Strauss, an immigrant from Bavaria. Setting up shop in San Fransisco, California, during the California Gold Rush, he identified a need for durable workwear.

This led to a collaboration with tailor Jacob Davis, resulting in the invention of the iconic Blue Jeans in 1873. Worn initially exclusively by gold miners, these jeans soon found favor with Hollywood starlets like Marilyn Monroe, marking the beginning of their iconic journey through popular culture.

Price range: $50 – $128

Coach

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

Price range: $35 – $750

Guess

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

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

• Dresses

• Handbags

Price range: $25 – $500

Nautica

Nautica is one of the best preppy clothing brands for warm weather style. It was founded in 1983 to design nautical-inspired clothes (hence the name). Nautica offers a suitable selection of preppy attire for the summer season.

Price range: $8 – $85

Hugo Boss

Hugo Boss is more than just a preppy brand for gentlemen. This German brand also has great pieces for women. You will be satisfied with the wide selection of modern and classy pieces!

Price range: $35 – $600

Cole Haan

You might have yet to hear of Cole Haan, but you will want to shop there when you see the brand's timeless footwear. Cole Haan was established in 1928 to offer:

• Excellent craftsmanship

• Comfort

• Design

Cole Haan Footwear

Cole Haan has created shoes with a traditional American style and bold innovations for nearly a century. From loafers, ballet flats, espadrille sandals, and Oxfords, the brand has preppy footwear for:

• Formal occasions

• Casual outings

You’re guaranteed to find polished shoes for your preppy wardrobe.

Price range: $90 – $425

Loewe

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

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

Price range: $300 – $3000

Mango

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

• Sweaters

• Loafers

• Classic sunglasses

Price range: $18 – $650

River Island

Another brand to have on your fashion radar is River Island. This iconic British high-street brand was founded in 1959. Heritage styles and modern influences inspire it. The brand offers classic silhouettes that will perfectly align with your preppy style. These include:

• Intelligent blazers

• Tailored pants

• Button-down shirts

Price range: $10 – $200

Club Monaco

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

Price range: $32.50- $950

Frank and Oak

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

Some of the most popular items from Frank and Oak are:

• Bermuda shorts

• Striped bubble cardigans

• Relaxed blazers

• Straight-leg jeans

Price range: $10 – $600

L.L.Bean

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

• Sweaters

• Sandals

• Jeans

Price range: $20 – $180

Gap

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

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

• Classic white tees

• Sweaters

• Cardigans

• Shirts

Price range: $18 – $230

LOFT

Get ready to be obsessed with the modern and feminine pieces at LOFT. This brand has everything you need to create that effortless, preppy, and girly style. Loft offers:

• Spring tweed jackets

• Striped poplin dresses

• Rugby collared sweaters

• More charming clothes

Price range: $19- 180

Draper James

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

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

Dudley Stephens

Step up your style with Dudley Stephens, a women-led brand that caters to the modern woman’s preference for classic styles over fashion trends. Dudley Stephens is committed to sustainability, crafting pieces that stand the test of time in recycled performance fabrics.

You will indeed find a piece that speaks to your classic style, from turtlenecks to pullovers, shorts, and more.

Hill House Home

Hill House Home should be the brand to explore for preppy clothes! The brand prides itself on celebrating life by offering exceptionally quality classic styles.

Experience the elegance of Hill House Home, a brand that embodies the preppy vibe with its elegant yet simple designs. Picture yourself in their pretty puff-sleeve dresses, a style that instantly transports you to the Hamptons. And don’t forget to check out their cool accessories, perfect for adding a touch of spice to your preppy outfits.

Tuckernuck

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

• Classic ballet flats

• Raffia tote bags

• Flowy dresses

• Polo shirts

• Tweed dresses

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Top 15 Preppy Photo Ideas to Try

1.  Picnic in the Park: A Picture-Perfect Scene

Set the scene with a classic picnic in the park. Lay out a plaid blanket, fill a wicker basket with goodies, and arrange your props. Grab a few books or a vintage camera for added detail. When it comes time to snap the pics, capture candid moments as you enjoy your picnic. 

Remember to include close-up shots of the details, such as your preppy outfits and picnic accessories.

2. Nautical by Nature: A Boating Photoshoot

Take your preppy photos to the water with a nautical-inspired boating shoot. Choose a crisp, bright day to capture the essence of summer. Dress in breathable fabrics that pair well with boat shoes or classic loafers. 

Opt for navy and white color combinations or bold stripes to enhance the sailing vibe. Accessorize with a captain’s hat or sunglasses, and pose on the boat and along the dock for various shots.

3. Tennis Anyone? Capture Classy Court Style

For a classic preppy photoshoot, it’s hard to beat tennis. The crisp white outfits epitomize a clean and classy aesthetic perfect for a summer day. Find a local tennis court open to the public and plan your shoot for early morning or just before sunset for gorgeous, diffused lighting. 

Dress in a coordinated tennis outfit and accessorize with a racquet and a few tennis balls. Get action shots of you playing a game and pose portraits for a balanced gallery.

4. College Campus Shoot: Channel Your Inner Ivy League Student

What’s more preppy than a college campus? If you want a classic and timeless setting for your photoshoot, head to your local university. Ivy League schools are lovely, with:

• Stunning architecture

• Manicured lawns

Back-to-School Photo Shoot

Aim for a late summer or early fall shoot to capture the essence of back-to-school season. Dress in your best preppy outfits, focusing on layered looks that include:

• Cardigans

• Blazers

• Stylish scarves

Bring props like books and vintage suitcases to enhance the collegiate vibe.

5. Beach Bonfire: Cozy Up for Fall

Plan a beach bonfire shoot with your friends if you’re lucky enough to live near the coast. This preppy photoshoot idea perfectly blends summer and fall as you transition into cooler weather. Start by dressing in:

• Cable-knit sweaters

• Classic loafers

• Colorful chinos

• Tailored shorts

Aim for dusk when the lighting is soft and flattering. Capture the details of your shoot, including: 

• The fire

• Your cozy blankets

• Colorful marshmallows before snapping a few posed shots

Then, get candid as you enjoy the evening and roast marshmallows for s’mores.

6. Croquet Anyone? Capture Classic Sport Style

Like tennis, croquet is another classic summer sport with a sophisticated vibe. If you can’t find a local match to crash, set up your backyard croquet course for your preppy photoshoot. Dress in your best preppy outfits—think pastel colors, summer dresses for women, and tailored shorts with polos for men. 

Accessorize with a vintage croquet set and get a mix of posed and candid shots to showcase your style.

7. Fall Foliage: Capture Vibrant Autumn Colors

As summer winds down, there’s nothing quite like fall foliage. If you’re looking for a stunning backdrop for your preppy photos, don’t forget to include fall colors in your planning. Aim for a local park or wooded area known for its vibrant autumn colors. 

Then, dress in layered preppy outfits with:

• Warm sweaters

• Scarves

• Classic boots for a cozy fall look

8. Country Club Shoot: Live the Preppy Dream

Every preppy dream of life at the country club. Capture the essence of this lifestyle in your photoshoot by dressing in your best golf or tennis attire and heading to your local country club for an afternoon of photos. 

Be sure to snag a few shots of the manicured greens, along with photos of the porch of the clubhouse.

9. Vintage Bikes: Capture a Classic Look

For a fun and playful preppy photoshoot idea, grab a couple of vintage bikes and hit the road. Choose a scenic route or a local park with paved paths for easy riding. Dress in classic preppy outfits—think:

• Colorful pastels

• Tailored shorts

• Cable-knit sweaters

Aim for a mix of candid and posed shots as you ride your bikes and capture the essence of a warm summer day.

10. Library Scene: Get Scholarly with Your Shoot

If you’re looking for a unique setting for your preppy photos, don’t forget to check out the local library or an old schoolhouse. Both locations provide the perfect backdrop for a scholarly shoot that channels your inner nerd. 

Dress in your best studious outfits, like plaid skirts with cardigans and knee-high socks, and hit the stacks for your photos.

11. Lakeside Dock: Capture Nautical Style

For a classic lakeside look, head to your local lake for a nautical-inspired shoot. Dress in breathable fabrics that look great layered, like your favorite striped shirt and a light-weight pullover. 

Grab a couple of props for your photos, like boat oars and a few life jackets, and get a mix of candid and posed shots as you enjoy the day at the lake.

12. Tailgating Scene: Show Your School Spirit

Celebrate your school spirit with a preppy tailgating shoot. Gather your friends and plan the perfect photoshoot before the big game. 

Dress in your best team colors, bringing props like pom and banners to enhance the scene. Capture detailed shots of your preppy outfits before getting candid as you enjoy the festivities.

13. Equestrian Inspired Shoot: Saddle Up for Style

Equestrian-themed photoshoots are a classic preppy staple. Wear your best riding attire for this shoot and head to your local stable for photos. You’ll find a horse to pose with for your photos if you're lucky. 

If not, don’t worry. Your shoot should capture the essence of equestrian style, which will deliver the preppy look you’re after.

14. Vineyard Tour: Capture the Essence of Sophistication

Wine country is a beautiful backdrop for any photoshoot, especially a preppy one. Dress in your best vineyard tour outfits to capture the essence of sophistication in your shoot. 

Think pastel-colored chinos, button-downs, and lightweight sweaters for men and airy summer dresses for women. As you enjoy the scenery, aim for a mix of candid and posed shots.

15. New England Coast: Capture Nautical Style

For a classic preppy photoshoot, head to the coast of New England. This area is known for its beautiful waterfront towns and stunning nautical scenery. Spend the day exploring the area:

• Dressing in your best nautical-inspired outfits

• Capturing the scenery

Don’t forget to include some close-up shots of your outfits and the details of the town in your gallery.

Why Preppy Photos Are Trending

Preppy Fashion: The Style Revival That’s All About Timelessness

Preppy fashion is timeless, sturdy, and classic. It’s well made. Everyone looks good in:

• Big, crispy pants

• Tweed blazers over sweater vests

• Cashmere twin sets

It might not make you look cool, but as Ralph Lauren taught us, you can put your spin on it by wearing cowboy boots, or a tie as a belt, or tying your cardigan around your waist like a weird little skirt, and—ta-da!—suddenly you’re an eccentric with formidable personal style.

Prep as a Refuge

You can see what might draw shoppers and women simply seeking to evolve their style to its foundations at a moment when so many trends exist and so much clothing feels cheap or disposable. Prep lasts. Prep is quality, and its fundamentals can be acquired for a reasonable price. 

Prep is the basic palette of style. And yet, that means that prep is conservative. It is a standard to which we’ve retreated in the face of this fashion chaos—all of us looking at these micro trends and fast fashion and thinking, we used to be a country, a proper country! And running to the reliable basics that made Muffy look so spiffy.

Old Money TikTok and the Allure of Preppy Style

About a year and a half ago, Old Money TikTok became a phenomenon. However, it’s still going strong, with figures like a woman who goes by Kiki Astor demystifying in a dud English accent what old-money types wear: 

• L.L.Bean Boat and Totes instead of Chanel handbags

• Barbour jackets instead of Blair Waldorf plaids

As someone who grew up in Delaware, the family seat of the du Pont family and the Bidens, I certainly have my own opinions about that—which is not to suggest my authority over hers, but rather to convey how varied or localized these status symbols are. Why is it that liberal young people are clinging to these reactionary clothes? Many of the Old Money TikTok videos adopt the Kiki Astor tenor: You all have it wrong, and let me tell you what real wealth looks like.

Prep and Class Fetishism

It’s anthropological—a digital-first sequel to The Preppy Handbook—but it constitutes a strange fetishization of class and wealth when, hey, I thought we all hated those people now! Just as many people use social media to criticize the way class and privilege work in America, as they do to celebrate how it looks. 

So why is it that young people, who, unlike their parents, are getting more liberal as they age, are clinging to these reactionary clothes? It is time to disregard conventional fashion norms.

Trend Reporting and Preppy Style

Beneath the surface of the contemporary preppy resurgence lies a complex phenomenon that eludes conventional trend analysis. While trend reporting often simplifies cultural complexities into easily digestible formats, the multifaceted nature of prep reveals the limitations of such oversimplification. 

The contradictions inherent in the preppy aesthetic challenge the tendency to reduce complex social and stylistic phenomena to superficial trends. Beneath the apparent conformity of preppy style exists a potential for fresh, unconventional interpretations that defy easy categorization.

Redefining Preppy Style

Contrary to popular perception, the contemporary preppy aesthetic deviates significantly from traditional stereotypes associated with the term. Leading fashion houses have reimagined the preppy look, infusing it with modernity and sophistication. Prada's interpretations of preppy elements are characterized by innovation and optimism rather than:

• Nostalgia 

• Conservatism

Saint Laurent's reimagining of classic preppy garments, such as cashmere and wool coats, demonstrates a contemporary approach that blends tradition with edgy allure.

Prep in High Fashion

The garments exhibit a sense of confidence and sophistication rather than androgyny. The contemporary aesthetic defies traditional notions of conservatism. Notably, even avant-garde designers incorporating preppy elements into their collections highlight the enduring influence of this style.

A New Look at Preppy Style

Thom Browne has convinced generations of men that wearing a skirt is a ball. Bode, which encourages consumers to think of themselves as custodians of heirloom garments, sculpts antique quilts into the straightforward, American workwear shapes that Brooks Brothers looked to in the 1920s; the brand’s designer, Emily Adams Bode Aujla, is looking to evening clothes from that period for her womenswear, conjuring a time when a woman’s beaded or drop-waist dress could signify that she was a rebel, an iconoclast, or even a political dissenter.

Prep as Cultural Critique

In the United Kingdom, brands like JW Anderson, S.S. Daley, Chopova Lowena, and Wales Bonner all use school uniform tropes and tailoring to reveal more profound, more complex (and at times painful) histories behind the societies that have upheld those garments as a kind of fashion beacon. 

In other words, the brands that perhaps most fundamentally shake the foundations of fashion would almost universally be preppy. But rather than reinforcing the lifestyle of prep and its trappings, they are swatting at them, playing with them, questioning them. Prep is back, and this time, it’s personal!

Preppy Style's History and Cultural Significance 

“Button-downs, khakis, and crewneck sweaters have a long history as a uniform of revolt, as author Jason Jules puts it, for Black Americans.” This is one of the downsides of trend-brain: We distill our understanding of a past aesthetic into the most digestible or immediate form, compressing out the:

• Beautiful

• Complicated

• Weird stuff in the process

As one of the best books on the history of prep, Black Ivy, articulates (coinciding with the prep renaissance, the book was released in 2021), preppy clothes are not nearly as white and exclusive as we might imagine. As author Jason Jules puts it, button-downs, khakis, and crewneck sweaters have a long history as a uniform of revolt for Black Americans.

Prep as Resistance

Another provocative dissection of the preppy uniform appears in The Andy Warhol Diaries, the 2022 documentary based on the artist’s daily journals. The film series is much more personal, and thus more queer, than previous Warholia. It argues that Warhol and longtime boyfriend Jed Johnson wore crewnecks, tweed blazers, and khaki slacks as, really, a kind of drag so that they could look normal but live and feel more openly in a period of grave animosity toward LGBTQ+ people. 

We find ourselves again in such a period, reviving the uniform’s power. In shows like Succession and The Revival of Gossip Girl, the approach to preppy or classic clothes and wealth is dark and twisted, even perverted. As my colleague Tara Gonzalez points out, it’s sexy. It’s as if the wearers of these clothes are taking the worlds, people, and ideas typically associated with them and purposefully messing with them. 

Prep's Evolution

The history of the sort of prep seen manifesting today is not:

• Abercrombie cargo pants

• Pink polos

• Mint juleps on the lawn

Diane Keaton exemplifies a complex and dynamic style approach, seamlessly blending avant-garde elements with classic preppy pieces. Her iconic 1994 Golden Globes ensemble foreshadowed contemporary fashion trends, demonstrating a prescient ability to combine traditional and experimental elements. This look anticipates the innovative and subversive approach of designers like Junya Watanabe and Chopova Lowena, who reinterpret classic fashion archetypes with a contemporary edge.

Prep Reimagined

Diane Keaton exemplifies a complex and dynamic approach to style, seamlessly blending avant-garde elements with classic preppy pieces. Her iconic 1994 Golden Globes ensemble foreshadowed contemporary fashion trends, demonstrating a prescient ability to combine traditional and experimental elements. 

This look anticipates the innovative and subversive approach of designers like Junya Watanabe and Chopova Lowena, who reinterpret classic fashion archetypes with a contemporary edge. Keaton, a prominent figure in fashion and film, embodies a unique fusion of:

• Avant-garde

• Preppy styles

Preppy Style Icons

Fonzworth Bentley, renowned for his impeccable taste, elevated the Atlanta preppy aesthetic to new heights. Princess Diana, a style icon, demonstrated the power of fashion as a form of personal expression and emotional resonance. Mick Jagger's distinctive blend of rebellious spirit and classic attire created a compelling and enduring image. 

Frank Ocean’s contemporary approach to fashion, characterized by unexpected juxtapositions of luxury and casual wear, further exemplifies the evolution of the preppy aesthetic. These individuals share a common ability to reinterpret and redefine traditional preppy elements, creating innovative and personal style statements.

Prep as a Canvas

Like the designers I mentioned, they use these extremely familiar clothes in unusual, exciting, and provocative ways. They challenge us to see what feels almost tired as special and individual, as the product of choice rather than peer pressure. Prep endures because its very recognizability presents some of our most creative and emotional dressers with the opportunity to challenge its values repeatedly.

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