You scroll through Instagram, and you can’t help but notice all the preppy images. The preppy aesthetic, with its clean lines and vibrant, classic patterns, is everywhere. From the color palettes to the patterns and styles, these photos have a unique vibe that feels fresh and cheerful yet simultaneously nostalgic. You're not alone if you’re drawn to this classic style but unsure how to achieve it. In this blog, we’ll break down what preppy images are, how to identify them, create your own, and find inspiration to help you incorporate this bright aesthetic into your style.

WhatColors’ AI personal color analysis app is a valuable tool for achieving your goals. It offers tailored recommendations to help you discover your unique color palette and identify the hues that will help you create cheerful, nostalgic, preppy images and outfit your next photo shoot.

Table of Contents

• What Are Preppy Images?

• Key Elements of Preppy Images

• 8 Iconic Preppy Image Examples

• How to Create Your Own Preppy Images

• Top 7 Resources for Preppy Images

• Try AI Personal Color Analysis For Free Today

What Are Preppy Images?

Preppy style has its roots in the affluent youth of the 1900s, whose fashion reflected their privileged lifestyles. As this group began to graduate from elite schools into society, their clothing became associated with the leisurely pastimes of the upper crust, such as:

• Sailing

• Tennis
  
  

Ivy League Preppy

The style became synonymous with the Ivy League, prestigious Northeastern universities, and the elite private schools that feed into them. Today, the preppy style evokes images of well-groomed students in:

• Cozy pastel sweaters

• Embroidered polos

• Crisp pleated skirts
  
  

It’s classic, colorful, and endlessly adaptable.

What Is Preppy Imagery?

Preppy images refer to visuals that embody the preppy style, which is characterized by clothing and aesthetics associated with affluent private school culture, particularly in North America. This style often includes elements such as:

Clothing

Typical preppy attire includes polo shirts, khaki pants, blazers, and boat shoes, reflecting a casual yet polished look. The style is often linked to activities like tennis or sailing, associated with elite social classes.

Aesthetic

The preppy aesthetic is colorful and often features patterns like stripes or plaids. It conveys a sense of wealth and privilege, frequently evoking images of:

• Well-manicured lawns

• Classic cars

• Upscale social events
  
  

Cultural References

Preppy images may also draw from cultural icons and media representations, such as characters from films and television who embody this style, like Blair Waldorf from Gossip Girl or characters from Pretty in Pink.

Timeless Staples

The preppy style is timeless. Cardigans, polo shirts, and Mary Jane shoes, all fashion staples, will never truly go out of style. American prep style has survived brand bankruptcies (J. Crew emerged from:

• Bankruptcy in 2020

• Store closures

• The rise of athleisure

• Hype beast trends
  
  

Its secret to remaining relevant? Preppy style has learned to adapt and evolve with the times.

What Are Common Themes in Preppy Imagery?

Overall, preppy images capture a lifestyle that is both aspirational and nostalgic, often appealing to those who appreciate its blend of:

• Tradition

• Modernity
  
  

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Key Elements of Preppy Images

Preppy style embodies classic elegance and a cultured aesthetic that evokes images of the Ivy League and old-school British colleges. The look conjures up a leisurely life filled with warm summer days, picnics on the quad, and afternoon sailing on the Sound.

Bright Aesthetics

Preppy images feature bright, cheery color palettes, neat and tidy outfits, and crisp settings like:

• Beaches

• Campuses

• Country clubs
  
  

The style is approachable yet exclusive and communicates a sense of heritage and tradition. 

Color Palettes of Preppy Aesthetic

The preppy aesthetic is characterized by its bright, airy color palettes. These outfits often feature crisp whites, pastel hues, and pops of color that evoke an atmosphere of:

• Affluence

• Leisure
  
  

Think sunny days on the coast or manicured lawns in the suburbs. The colors commonly associated with preppy style include light pinks, yellows, blues, and brighter shades like navy and greens. Outfits also incorporate classic neutrals like khaki and gray for balance.

Patterns and Textures

Preppy images feature bright, cheery colors and classic patterns and textures. Stripes, plaids, and argyle are among the most popular textures for elevating the look of preppy outfits. 

These can be incorporated through layering pieces like sweaters or blazers, accessories like scarves and ties, and even the main pieces of an outfit like:

• Skirts 

• Dresses
  
  

Accessories, Detailing, and Settings

Finally, the devil is in the details regarding preppy images. Crisp outfits are made all the more appealing with elegant accessories like:

• Pearls

• Leather goods

• Sporty watches
  
  

Settings play an integral role in the preppy aesthetic. Pictures taken on college campuses, beaches, and country clubs capture the leisurely lifestyle associated with this classic style.

Color Analysis by WhatColors

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8 Iconic Preppy Image Examples

1. Ralph Lauren’s Iconic Polo Campaigns

Ralph Lauren's Polo brand is synonymous with preppy style. Images from their campaigns often feature models dressed in classic blazers, polos, and chinos, set against backdrops like Ivy League campuses or country estates.

2. Jackie Kennedy: The Original Preppy Icon

Jackie Kennedy was a true preppy. She grew up in a wealthy family, attended top private prep schools and colleges, and loved horse riding. 

Although preppy fashion has evolved over time and looks a little different from the past, Jackie Kennedy played an important role in defining and popularizing it. She often wore shift dresses and pearl jewelry, considered the essentials of preppy style.

3. Blair Waldorf from Gossip Girl: Modern Preppy Style

Blair Waldorf, played by Leighton Meester, is a modern preppy icon. Images of her in tailored skirts, headbands, and elegant blouses, often set in the Upper East Side or private school settings, have influenced countless preppy looks.

4. JFK’s Sailing Photos: Preppy Style at Play

It may be hard to imagine, with a White House filled with shiny red ties and tanning beds, that a president could ever now be considered a style icon. With John F. Kennedy, the youngest and most dashing of all the Commanders-in-Chief, style oozed from the Oval Office like tweets from a narcissist. 

JFK was never the most perfectly groomed or sharply tailored of presidents (and he certainly didn’t stand on ceremony to passing fads). But in his louche, simple, profoundly functional wardrobe, he led from the front in a way no president has done since. In the Quad, a great deal of JFK’s style was formed among the cloisters and ivy of Princeton, his Alma Mater.

Kennedy's Style

Though a hint of the president’s 1930s upbringing lingered at university through some double-breasted stroller suits, JFK largely embraced the classic, laid-back, athletic traditions of the Ivy League wardrobe. The president was known to wear striped “rep” ties and more bookish knitted numbers throughout college, often with oxford shirts and Brit-inflected tweeds. 

Even after he left, while beginning to make maneuvers on his political career, the man enjoyed a relaxed and gently disheveled wardrobe – corduroy or worsted blazers with:

• Chipped and broken buttons

• Casual chinos with turn-ups

• Slightly battered boat shoes
  
  

Kennedy's Style

JFK wanted to remain well-dressed—a man of the people, never a member of the East Coast metropolitan elite. At Work, he had begun to refine and rethink his style by the time he was installed in the grandest political office. 

Gone, mostly, were the striped and knitted ties of his youth, and in came the simple, block-color silk numbers that defined his crisp look. (When he was assassinated, JFK wore a dark blue silk tie from Christian Dior.) This development, at least, was a nod to fashion – JFK favored ties slightly on the slimmer side, in the style of the late fifties and early sixties.

Oval Office Style

Kennedy’s Oval Office uniform consisted overwhelmingly of a white, point-collar shirt beneath a solid dark blue or grey suit (though on some occasions the president sported a subtle pin stripe or a very vague check). 

Kennedy wanted to be perceived as an enduring and trustworthy statesman, and his suits reflected this workmanlike image – the shoulders had little padding, were slim and straight, and often had no vents. They were always from Brooks Brothers – honest American tailoring for the honest American man.

Casual Kennedy

Though he was presented with a top hat at his inauguration, the president was never seen in it. He declined to wear formal hats altogether, a choice that undoubtedly played some part in the accessory’s decline across the 1960s. At Play, the most enduring images of JFK are those of the man at ease and playing.

One of Kennedy’s greatest loves was his sailboat Victura, a gift from his father at age 15. This nautical influence bled into many of his fashion choices, giving the young President a lightly preppy, summery lean throughout the year. Kennedy favored polo shirts – long and short-sleeved in white, blue, or grey – below heavy knit sweaters and preppy cardigans.

Layering Styles

The president would fight off the New England wind on deck with a G-1 Flight Jacket – a functional, fleece-collared version of the later bomber. Once ashore, Kennedy would opt for cream or khaki chinos below classic Oxford shirts and ties, perhaps layered neatly with a crewneck sweater. 

On the floor – penny loafers, docksiders, or scuffed white plimsolls. But the most commonly emulated trait of this great and natural man of style is:

• Based

• Curiously

• Misapprehension
  
  

Sunglasses Style

The tilted, tortoiseshell sunglasses that came to define the serene, stately cool of the era were not, in fact, Rayban Wayfarers. Style historians have pinpointed the American Optical TC74-51, the Cabana TS 2505, and the Universal Optical “Mansfield Square” glasses as the president’s favorite pairs instead. But details, details. JFK himself – relaxed, pragmatic, unassuming – wouldn’t have minded a jot.

5. The Cast of Dead Poets Society

The 1989 film Dead Poets Society is full of preppy imagery. It portrays students at a prestigious all-boys prep school, and the uniforms, blazers, and classic academic settings all contribute to a timeless preppy aesthetic.

6. Tommy Hilfiger’s All-American Campaigns

Tommy Hilfiger has long been associated with preppy style. His All-American campaigns, featuring models in red, white, and blue outfits with varsity jackets, boat shoes, and crisp button-downs, perfectly capture the essence of preppy imagery.

7. Princess Diana: The Preppy Style Queen

Princess Diana’s fashion evolution can only be described as legendary. Even decades after her tragic death, it’s impossible to ignore the Princess of Wales’s ongoing impact on the world of style. The royal, who would have turned 63 today, inspires millions with her:

• Philanthropic work

• Distinctive personal expression
  
  

Diana’s looks are so famous that they come with unique names and stories of their own; they’re some of the most talked-about outfits of all time. The revenge dress, the Travolta dress, that fairytale, David- and Elizabeth Emanuel-designed wedding dress—each stands out as a distinct pop culture moment.

Princess Style

Pre-fame, she stuck to “Sloane Ranger” staples like preppy sweater vests, printed midi-dresses, and equestrian boots. Once she became a princess, Diana switched gears and began to rely on trusted designers like:

• Catherine Walker

• Anya Hindmarch

• Murray Arbeid to create exquisite custom pieces
  
  

Statement-making gowns were Diana’s calling card. Whether she was attending a performance of The Phantom of the Opera in a strapless navy ball gown by Arbeid covered in silver stars or wearing a Catherine Walker taffeta number with a gathered skirt at a society gala in Melbourne during the Australian tour she and Charles undertook in 1988, Diana embodied the ideal of the princess, even when her life was far from that fantasy.

8. Kate Middleton: Modern Preppy Style

Princess Kate might be associated most strongly with sequin gowns, sparkling tiaras, and shiny baubles, but she’s most frequently found in striped sweaters and sleek blazers. For years, Kate has been dedicated to collegiate chic styles often of:

• Cable knit sweaters

• Pleated skirts 

• Gingham button-downs
  
  

She’s never said no to a banded boatneck or passed on a pinstripe. Kate has mastered the art of Ivy League attire for the princess set but how does she pull it off? Here are 8 Ways Kate Middleton Perfects her Preppy Outfits:

1. She Sticks to a Theme 

If you’re going for athletic prep, stick with it. College chic, don’t deviate. Miss Maritime, keep it up. The princess always commits to a preppy theme case in point Sailor Styles; she’s known to wear lots of nautical motif ensembles and follows through on her commitment to the aesthetic such as:

• Shaded navy blue handbags

• Life ring earrings

• Heritage lace detailed boat shoes
  
  

2. She Goes Casual 

The preppy dressing doesn’t have to be frumpy or fancy—a simple striped Breton boatneck and a pair of skinny jeans make a complete outfit. Kate loves embracing Hamptons Daywear, like this Americana navy and red striped pullover from Italian label Luisa Spagnoli paired with dark wash denim and plimsoll sneakers from Sugera. 

3. She Embraces Her Sporty Side 

A patron of rugby and tennis organizations, Kate must keep a bit of prep in her step. She remains loyal to her patronages by donning their uniforms from rugby competitors in tracksuits and sneakers to tennis champs in pleated mini skirts that scream boarding school rebel. 

4. She Craves Cableknits 

Preppy fashion can be as simple as a cricket sweater with striped accents and a pair of slacks. The princess has mastered this fuss-free fashion statement with plenty of prep, often donning her cable knit jumpers for relaxed royal engagements. 

5. She Makes Sitcom Dad Vests a Staple 

Once reserved for recliner-inclined grandpas or suburban sitcom dads, the sweater vest has emerged from its geeky reputation and has been wholly embraced by the cool celebrity crowd. 

From Kendall Jenner in a retro Mango multicolored gilet to Dua Lipa in a strawberry-printed tank vest to Gigi Hadid in an argyle crop, the sweater vest is not to be forsaken. Kate has recently revisited her preppy past in a funnel-neck jumper made for back-to-school. 

6. She Knows a Sailor Shoe is Required 

Before she lived in her Mint Velvet Bibi trainers and Superga sneakers, the princess was rarely caught doing down-to-earth dressing without her Sebago Bala Taupe Boat shoes. The moccasin-constructed leather “old money” shoes have a country club flair that gives them plenty of preppy personality. 

7. She Learned to Love a Loafer 

Kate loves a preppy shoe look from Russell & Bromley. She covets their tassel-accented navy loafers and snaffle-trimmed menswear-inspired styles. She’s left behind her red Crocs and sheepskin Uggs in favor of these classic, intelligent shoes. 

8. She Embraced the Charm of the Blazer 

The princess loves a layered look with plenty of preppy panache. She can’t resist this ultimate in student dress code from gingham shirts to checked styles and plaid prints–a single-breasted blazer over an oxford shirt. 

Carrying on this alumni aesthetic's classic and conservative nature, she always looks ready to hit the books.

How to Create Your Own Preppy Images

Start with the Wardrobe: Preppy Essentials Clothing

The foundation of any preppy image is the wardrobe. Classic pieces like button-down shirts, polo shirts, chinos, cable-knit sweaters, blazers, and A-line skirts are must-haves. Opt for:

• Pastel colors

• Navy

• White

• Muted tones
  
  

Patterns like stripes, plaids, and argyle are quintessential to the preppy look.

Accessories

Accessories are key to enhancing the preppy vibe. Pearls, leather belts, loafers, boat shoes, and headbands are all iconic preppy accessories. 

Sunglasses with wayfarer or aviator frames, along with simple yet elegant jewelry, add a touch of sophistication to the outfit.

Pick the Perfect Backdrop for Your Preppy Shoot 

Ivy League universities and private school campuses are classic backdrops for preppy images. Think brick buildings, manicured lawns, and grand libraries. 

• Coastal Scenes: Beaches, sailing clubs, and docks are perfect for a more nautical preppy look. The natural light and relaxed vibe of a seaside setting complement the preppy style. 

• Country Clubs and Estates: Golf courses, tennis courts, and stately homes provide an elegant and luxurious setting that enhances the preppy aesthetic. 

• Urban Chic: For a modern twist, urban settings like upscale neighborhoods, classic brownstones, or chic cafes can serve as great backdrops while still maintaining a preppy vibe.
  
  

Focus on Posing and Composition Classic Poses

Keep the poses relaxed but polished. A confident stance with hands in pockets, a casual lean against a wall, or a natural laugh can convey the effortless elegance of preppy style. Group

Shots

If you’re photographing multiple people, arrange them to showcase the symmetry and balance typical of preppy images. Imagine a group of friends at a picnic, all dressed in coordinating preppy outfits.

Close-Ups

Don’t just focus on the full outfit; capture the details that make the preppy look unique. Close-ups of accessories, shoes, or the texture of a cable-knit sweater can add depth to your images.

Lighting and Filters: How to Set the Mood for Preppy Images

• Lighting and Filters Natural Lighting: Preppy images often have a bright and airy feel. Shoot in natural light whenever possible, preferably during the golden hour (early morning or late afternoon) for a warm, soft glow. 

• Editing: Using filters that enhance the natural colors without over-saturating them. Soft pastels and slightly muted tones work well for preppy images. 
  
  

Avoid heavy contrasts or overly dramatic effects, as these can detract from the clean, classic look.

Attention to Detail: The Preppy Touch Props

Props can help to set the scene and reinforce the preppy theme. Items like books, tennis rackets, vintage bikes, or picnic baskets can add a charming touch to your images. 

• Coordination: Ensure that all elements in the image are cohesive. The clothing, accessories, setting, and poses should all convey a unified preppy aesthetic. 

• Backgrounds: Pay attention to the background of your images. A cluttered or overly busy background can distract from the preppy vibe. Opt for clean, simple backgrounds that complement the subject.
  
  

Crafting the Story: How to Tell a Narrative with Preppy Images

• Crafting the Story Narrative: Preppy images often tell a story, whether it’s a day at the club, a stroll through campus, or a summer afternoon by the sea. Think about the narrative you want to convey and how your images can capture that story. 

• Authenticity: While the preppy style is polished, it should feel authentic and lived-in. Avoid making the images too posed or artificial; aim for a natural, effortless look that captures the preppy lifestyle.
  
  

Incorporate Seasonal Themes, Fall and Winter

For colder months, focus on layering with tweed blazers, wool coats, and scarves. The colors can be more prosperous, with burgundy, forest green, and deep navy prominent. 

• Spring and Summer: During warmer months, lighten the wardrobe with crisp whites, light linens, and pastel hues. Outdoor settings like gardens or beaches work best during these seasons.
  
  

Experiment with Different Preppy Styles Classic Preppy

Stick to traditional elements like polo shirts, blazers, and chinos. The overall vibe is timeless and conservative. 

• Modern Preppy: Introduce contemporary twists, such as slimmer fits, trendy accessories, or bold patterns, while maintaining the core preppy elements. 

• Sporty Preppy: Focus on athletic-inspired looks, like tennis whites, rugby shirts, or sailing attire. This style is more casual and energetic but still polished.
  
  

Style Evolution

WhatColors helps you find what colors to wear based on your skin tone. Finally, our patented color match technology lets you get your season based on your skin tone. Get the perfect colors based on your season. Avoid colors that are a definite no. Based on your skin, eye, and hair color, find the perfect nail colors with our WhatColors nail color generator.

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

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Top 7 Resources for Preppy Images

There are numerous resources available for finding preppy images, which encompass a variety of styles and themes. Here are some notable options:

1. Freepik

Offers over 31,000 preppy aesthetic images, including vectors, stock photos, and PSD files, that are free for commercial use. This platform is ideal for graphic resources related to the preppy aesthetic.

2. Wallpapers.com

It provides over 200 preppy aesthetic pictures that can be downloaded for free. These images are suitable for personalizing devices or creative projects.

3. Unsplash

This site features a selection of more than 100 free preppy images that are copyright-free and available for commercial use. It is great for high-quality photographs that fit the preppy theme.

4. iStock

Contains a vast library of over 416,000 preppy stock photos and images, making it a comprehensive resource for those seeking specific preppy visuals, including:

• Fashion 

• Lifestyle images
  
  

5. Shutterstock

Shutterstock has a large collection of over 400 million images, including many that fit the preppy aesthetic. You can find photos of models wearing classic preppy outfits, as well as lifestyle shots that capture the preppy vibe.

6. Etsy

Check out our preppy pictures for wall selection for the very best in unique or custom, handmade pieces from our digital prints

7. Pinterest

What is the perfect preppy look? This board can give you the inspiration for the perfect preppy outfit!

Try AI Personal Color Analysis For Free Today

Choosing the right colors can make or break an outfit. Color can make a statement, set a mood, and create visual harmony. Color is so important that it can even alter the perceived temperature of an outfit; a collection of cool tones will make a much different visual than a grouping of warm hues, and the two will conjure different associations that can impact how onlookers respond to the wearer.

Color Harmony

The preppy aesthetic has a distinct color palette; avoiding it can harm your success in nailing this style. WhatColors helps you find what colors to wear based on your skin tone. Get your season based on our patented color-match technology. Get the perfect colors based on your season. Avoid colors that are a definite no. Based on your skin, eye, and hair color, find the perfect nail colors with our WhatColors nail color generator. 

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

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