Preppy pictures offer the perfect inspiration if you want your photos to showcase your most stylish self. The preppy aesthetic is one of the most distinct and recognizable styles, capturing the essence of timelessness. This blog will dive into the preppy style and share examples to inspire your next photoshoot. 

Learn more about the style and see examples to inspire your next preppy photoshoot. WhatColors’ AI personal color analysis app can help you identify your color palette to ensure your next preppy pictures are as stylish as possible.

Table of Contents

• What are Preppy Pictures?

• 5 Characteristics of Preppy Pictures

• What Colors Are Typically Used in Preppy Pictures?

• Are There Specific Types of Clothing Often Featured in Preppy Photos?

• 7 Preppy Outfit Staples

• How Can I Style My Outfit for Preppy Pictures?

• What Are Some Common Settings for Preppy Pictures?

• Where Can I Find High-Quality Preppy Wallpapers?

• Standout Celebrity Preppy Looks To Inspire Your Next Look

• Try AI Personal Color Analysis for Free Today

What are Preppy Pictures?

The preppy aesthetic is a clean, classic style associated with the Ivy League and elite prep schools. Originating in the 1900s, it is polished and sophisticated, featuring timeless fashion pieces like:

• Cardigans

• Blazers

• Polo shirts
  
  

The aesthetic is not solely about looks—it embodies a particular lifestyle. Preppy pictures showcase the classic style while highlighting the wealth, privilege, and education often associated with this aesthetic.

The Origins of Preppy Style

The roots of preppy style date back to the 1900s, when the elite who attended Ivy League and preparatory schools began to develop their signature looks. Naturally, their wealth afforded them access to the best clothing of the time, which included garments like:

• Brooks Brothers button-downs

• Knit sweaters

• Loafers

By the 1930s, college women were in on the trend, and denim entered the preppy aesthetic.

The 1950s: A Mid-Century Expansion

Preppy style expanded in the 1950s and seeped into pop culture. Movies like Grease and Pleasantville featured the classic looks. During that decade, they also ushered in sporty rugby shirts and plaid patterns. 

The 1980s: The Official Preppy Handbook

By the 1980s, the preppy aesthetic was a fully formed style we recognize today. The rise of a book called The Official Preppy Handbook, along with pop culture icons like:

• Brooke Shields

• Princess Diana

• Their classy looks
  
  

This has propelled preppy style into the mainstream. The era’s wealth of catalogs and magazines made it easy for everyday folks to replicate the looks.

The 1990s: A Shrunken Twist

The late 1990s brought a new, skinny twist to preppy style. Pant styles were lower, and boot cuts were in. While oversized grunge had its moment, preppy elements like plaid and knotting shirts remained. 

The 2000s: J.Crew and the Rise of Athleisure

In the early 2000s, Jenna Lyons at J.Crew began to shake things up. She made us think of preppy style as shockingly bright colors, tons of sparkle, and playful twists. As the 2010s approached, another shift occurred, and athleisure arrived. 

The "New" Preppy Look

During Fashion Week, collections clarified that the preppy style has undergone yet another metamorphosis. Shows like Chloé and Michael Kors featured mid-length skirt suits; Burberry had collegiate sweaters; Versace broke out the rugby stripes; and Dior included a ton of plaid and neckties. Those styles have already hit the streets as people are back knitting their sweaters and reaching for pairs of chinos. We're seeing collars again, vests, and argyle, as well as other iconic preppy prints.

Related Reading

• Preppy Clothes
• Preppy Outfits
• Preppy Style
• Preppy Girl
• Preppy Photos
• Preppy
• Preppy Room
• Preppy Stuff
• Preppy Nails
• Preppy Bedroom

5 Characteristics of Preppy Pictures

1. Color Palette: The Fresh Hues of Preppy Pictures

Preppy style relies on a bright, cheerful color palette. Preppy pictures often feature light and pastel colors, especially pink, blue, and green. You might see a classic combination of soft pink with navy blue and crisp white or a summery palette of yellow and turquoise. The look is fresh and clean, evoking a sense of classic coastal elegance.

2. Fashion Elements: Polos, Khakis, and Other Preppy Staples

When you look at preppy pictures, you’ll notice the outfits are always polished and put together. There are no frayed hems or wrinkled fabrics in sight. Preppy pictures capture a particular lifestyle, and the clothing reflects an upper-class, traditional vibe. 

Classic preppy attire includes:

• Polo shirts

• Blazers

• Khakis

• Cable-knit sweaters

• Stripes
  
  

3. Settings: Capturing the Good Life

Preppy pictures are often set in idyllic environments that reflect the luxurious lifestyle of the upper class. Think university campuses (e.g. Princeton University), upscale neighborhoods, or picturesque outdoor settings. You might also find preppy pictures taken at country clubs or along the coast, where the aesthetic truly shines.

4. Poses and Expressions: Confident and Carefree

In preppy pictures, the subjects look incredibly cheerful and ideally at ease in their surroundings. They have fresh-faced smiles and pose confidently in their attire, as if they know they’re the star of the show. 

5. Accessories: Details to Elevate the Look

Preppy pictures are often styled with accessories that further enhance the classic aesthetic. For example, pearls, boat shoes, or colorful, personalized monogrammed items might be seen. Other standard details include stylish backpacks, glasses, and pop-of-color belts. 

What Colors Are Typically Used in Preppy Pictures?

The color palette of preppy pictures draws on strong, classic hues. The iconic color scheme of this aesthetic is pink and green, à la Lilly Pulitzer apparel (a prep staple if ever there was one). But navy, red, pine green, mellow gold, and rich and leathery browns are equally appropriate.

These traditional colors convey a sense of refinement and timelessness as they evoke the elite yet understated New England style. However, you don’t have to go overboard and drench a room in your chosen color scheme. A healthy dose of white balances the brilliant pink and soft green in the bedroom above to make them feel more of the moment.  

Monogrammed Pictures: A Preppy Staple

Monograms pop up on everything from bed and bath linens to barware and throw pillows in preppy pictures — a discreet (or not so discreet) mark of pride in one's name and heritage. What's preppy style without monograms? Give monograms a fresh spin with mod-looking fonts and fun colors. Or consider monogramming unexpected objects, such as chair backs. 

Nautical Accents in Preppy Pictures

Boating goes hand in hand with the classic preppy lifestyle, so maritime touches are de rigueur in preppy pictures. You can't go wrong with nautical stripes, maps, or prints — just avoid overdoing it and ending up with an elaborate space. 

Preppy is never kitschy. Keep these accents simple and graphic. For example, a display of framed nautical flags hung in a grid would lend an appealing graphic punch. Or focus on a few simple, standout elements, such as the oar, rope knot, and model sailboat above. 

Vintage Accessories in Preppy Pictures

Preppy homes artfully celebrate their hand-me-downs and family heirlooms. Old steamer trunks, vintage suitcases, and more whisper of a worldly, well-traveled lifestyle. Items hinting at the sporting life, such as old tennis racquets or riding gear, feel pitch-perfect. Layer these objects judiciously in preppy pictures to avoid a mishmash or an overly themed space. In the bedroom shown here, suitcases are stacked casually to stand in for a night table, and the clean, crisp look that defines the rest of the space allows them to shine.  

The Timelessness of Blue and White China in Preppy Pictures

Blue and white china — ginger jars, plates, pitchers — is a preppy mainstay. Whether it's delft or blue willow, it's timeless enough to blend with virtually any palette and mix of furnishings. Instead of a traditional cluster of wall-hung plates or mass of jars on a mantel, arrange blue and white dishware in a more streamlined way in preppy pictures. Display it in an orderly grid, as in this dining space, or group just a few pieces on a tabletop or shelf. 

Are There Specific Types of Clothing Often Featured in Preppy Photos?

The preppy aesthetic revolves around the classic, clean-cut pieces you associate with old-school Ivy League style. When it comes to preppy outfits, think polished, put-together, and perfectly tailored. The style is about looking sophisticated, even if you just hang out at home. Key wardrobe staples of the preppy aesthetic include:

• Polo shirts

• Blazers

• Cable-knit sweaters

• Chinos

• Pleated skirts
  
  

These pieces are typically styled to emphasize neatness and a polished appearance. For example, a preppy outfit may feature a crisp, collared shirt or a cable-knit sweater layered over a button-up to create an organized look. Pieces like pleated skirts and chinos also evoke a sense of formality often present in preppy outfits. 

Americana Prep: A Patriotic Take on Preppy Style

Americana Prep is more completely American-focused in its aesthetic. Think Ralph Lauren, jeans, American flags, and polo players. This aesthetic is steeped in the preppy lore of the American traditions that were prominent at the turn of the century. A recent Coveteur article noted that American Prep is "Toeing the line between minimalist and maximalist. Often a tad patriotic, not only in style and hues, the American flag and 'USA' often make an appearance. Add a dash of Western, and you've got yourself a look." 

7 Preppy Outfit Staples

1. Pretty Pleats

A wardrobe staple that has always steered us right is a tennis skirt. Hitting at about mid-thigh to show off those stems, pleated mini skirts became a frenzy in the 90s. Surprisingly, this skirt is popular even today and is a go-to pick for many fashionistas– all thanks to its crisp, clean pleats that evoke a quintessentially preppy look. 

2. Polo

Sure, polos were an aughts staple, but they gained cult status because they are a perfect blend of sophistication and athleticism. It is no surprise that they are regarded as among the famous pieces of prep clothing.

3. Vintage-y Cable Knit Sweater

An easy preppy outfit that looks good on almost everyone is a cable knit sweater. So, it’s a must-have staple in your wardrobe. Combine a cable knit sweater with black jeans for an easy-breezy look. Or, pairing a hint of style with an untucked button-down shirt. After all, an untucked button-down shirt looks charming when worn under a cable knit sweater. Add a pleated skirt to the mix, and you’ve got a look that captures the essence of effortless coolness, the one that makes a preppy outfit a standout. 

4. Striped Separates

Stripes are the go-to pick for many fashionistas because they make almost any outfit interesting.
Create a prep fit by matching and mixing preppy materials and patterns with stripes. For a casual work day, toss a striped button-up shirt with blue denim. Or, throw on striped shorts with a cable knit v-neck sweater. Slip into a pair of metallic flats, which deliver prep but with a twist.

5. Rugby Shirt

Representing prep style at its core, a good rugby shirt looks gorgeous on almost everyone without being snobbish. Plus, it’s a versatile piece of clothing, as it can be styled on colder days and easy evenings. Aren’t these reasons enough to add a rugby shirt to your wardrobe?

Breaking the Mold

People often stick to jewel-tone and nautical (blue and white) color palettes for preppy aesthetic outfits. But that doesn’t mean you cannot mix things up. Ditch the classic way of styling a rugby shirt. Instead, opt for a brightly colored shirt and pair it with matching bike shorts—a fresh take on an old favorite.

Wear a waist-skimming crop or a puffy sleeve style for added flair and femininity. 

6. Prep Sweats

Did you know you can pull off preppy outfits with sweats? Many don’t, either, so you’re not alone. Since sweats make outfits preppy, why not give it a try? Put on your favorite:

• Sweats

• T-shirt

• Blazer, and tie a crewneck sweatshirt over your shoulders 
  
  

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

7. Trouser

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


Pair trousers with the coziest, fluffiest cardigan for a laid-back preppy vibe. A turtleneck sweater also looks great with trousers. Just make sure to go for the shade that complements the color of your pants. Round out your outfit with boots and a puffer jacket. 

How Can I Style My Outfit for Preppy Pictures?

The sweater vest is your must-have ally for conjuring an off-the-bat preppy outfit with minimal effort but maximum style points. This simple knit's beauty is that you can throw it over a classic Johanna Ortiz shirt and be out the door in minutes. Instead of opting for your standard straight silhouette, we encourage you to invest in an oversized style à la Anine Bing. 

The wide neck and relaxed structure bring a casual air to your preppy outfit that’s perfect for grabbing coffee with an old friend or an afternoon spent reading. Further, lean into this oversized aesthetic with a pair of wide-leg trousers that you can punctuate with some Gianvito Rossi Loafers. The key to this look is using your sweater vest as a foundational piece and building your preppy outfit around it.

Sporty Chic Outfits for Preppy Pictures

When you find yourself in need of a light stroll, try this sporty-chic outfit on for size. Characterized by a logo-print shirt reminiscent of the Ivy League toppers once worn by Princess Diana, this preppy outfit keeps comfort in mind.

Balance out the soft exterior of your cotton sweatshirt with a Thom Browne pleated skirt to bring some texture to your look, and make sure you match your loafers with your handbag. After all, it’s what any true self-appointed prepster would do.

Focus on Seasonless Foundations for Preppy Style

Due to the cyclical nature of fashion, it’s easy to fall into the trap of investing in outfits you won’t wear after a season or two. That’s why purchasing foundational pieces that speak to the preppy style trend and have a life afterward is essential. 

Burberry Trench Coat is a British staple, this overcoat is a topper that coincides with studious style (see its double-breasted design and structured collar) but also works as a standalone piece. If this doesn’t quench your intellectual thirst, opt for a pair of Celine glasses instead. Once enlisted in your wardrobe, you can dress them up or down (courtesy of Roger Vivier) as you see fit.

Smart Layering for Preppy Pictures

It’s not what you have but how you style it that defines an outfit—just look at Coco Bassey. The fashion maverick shows that straight-leg mid-wash jeans can look preppy when paired with a crisp white shirt and cashmere blend pullover. 

What we love most about this look is how the white shirt offers a bright contrast to the subdued hues of navy. Elevate this look further by adding a gold chain for an air of high-fashion decadence—you won’t regret it.

Modern Sophistication for Preppy Pictures

Over the seasons, designers have been reimaging preppy outfits in a new light. This is most apparent at Christian Dior, where Maria Grazia Chiuiri has taken this beloved aesthetic and given it a modern twist. The French label proves you can embrace sultry fabrications such as sheer mesh and leather while appealing to the scholarly vibe through signature silhouettes. This preppy outfit is for those who want to stand out.

Business Casual Preppy Looks

In a time where WFH is the new normal, it’s essential to have a uniform that reflects this shift—and what better place to start than Miu Miu? While the Italian label has built a reputation for pussybow blouses and delicate dresses, it introduced a plethora of low-waist tailoring. It cropped knitwear cast in dark hues for Spring/Summer 2022. The result? A collection that melds preppy style with relaxed sophistication. We implore you to decorate your new look with a bag from Miu Miu’s older sister, Prada.

Focus on a Statement Shirt for Preppy Pictures

Though the beret has long been associated with preppy style, we suggest trading your accessory for a statement shirt instead when bringing a certain je ne sais quoi to your outfit. Ganni’s Ruffled Two-Tone Organic Shirt adds color to your everyday look and texture. Lean into the bright hues with light-wash, wide-leg jeans that feel very Parisian, and finish your outfit with a pair of decadent Jimmy Choo’s—you won’t regret it.

Weekend Uniforms for Preppy Pictures

Even scholars have time off. So, when the weekend comes calling, we suggest trading structured shirts for delicate knitwear. Cormio’s Cotton and Wool-blend Cardigan's vibrant pink hue embodies that springtime feeling of escapinWhatColors’ AI Personal Color Analysis appg the city and exploring the countryside. Its crotched exterior and bow detailing create a preppy look that pairs seamlessly with a denim skirt and Chanel Pumps. 

Discover Your Perfect Colors with WhatColors

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.

What Are Some Common Settings for Preppy Pictures?

Ivy League College Campuses: The Academic Roots of Preppy Style

Ivy League college campuses capture the essence of preppy style. Their historic brick buildings, manicured lawns, and picturesque outdoor settings embody the academic origins of this classic look. Elements further enhance the preppy aesthetic:

• College crests

• Pennants

• Ivy-covered walls
  
  

Country Clubs and Golf Courses: A Taste of Leisure and Exclusivity

Country clubs and golf courses represent the leisurely side of preppy style. The well-maintained greens and clubhouses provide a polished backdrop for preppy pictures. In these settings, you might spot people in tailored sportswear cruising around on golf carts or preparing to play tennis or croquet.

Yacht Clubs and Marinas: Nautical Themes

Yacht clubs and marinas are another fantastic location for preppy pictures. Nautical motifs permeate the preppy aesthetic, which draws heavily from upper-class leisure activities. 

Common elements of this style are:

• Sailboats

• Deck shoes

• Striped patterns
  
  

The background of preppy pictures taken in a marina may include a harbor filled with boats or a clubhouse decorated with maritime decor.

Tennis Courts: The Quintessential Preppy Sport

Tennis is the most quintessentially preppy sport, and pictures taken at tennis courts enhance the look remarkably. Clay or grass courts offer an authentic backdrop for preppy pictures, while vintage wooden rackets, white outfits, and cable-knit sweaters create an instantly recognizable vibe.  

Equestrian Facilities: Horseback Riding and the Preppy Aesthetic

Horseback riding is another sport associated with upper-class leisure, and pictures taken at equestrian facilities capture the essence of preppy style. Contribute to the preppy aesthetic and offer an elegant background for preppy pictures:

• Stables

• Riding outfits

• Polished leather accessories
  
  

Upscale Beach Towns: Coastal Chic

Preppy style draws heavily from coastal looks, and upscale beach towns provide the perfect backdrop for preppy pictures—places like Martha's Vineyard feature weathered shingle houses, lighthouses, and beaches with dune grass. People might be seen in boat shoes, carrying canvas totes, or riding bicycles.  

Ski Resorts: Winter Preppy Style

Winter preppy style has a look all its own, and pictures taken at ski resorts beautifully capture this aesthetic's essence. Think log cabins, aprés-ski lounges, and people in designer ski wear or classic winter attire like cable-knit sweaters and tartan scarves. 

Picturesque Outdoor Settings: The Great Outdoors

Preppy pictures are sometimes captured in idyllic natural settings like sunny parks with lush greenery. These environments enhance the aesthetic and create a fresh, cheerful backdrop for any preppy photo shoot.

Related Reading

• Preppy Things
• Preppy Hairstyles
• Preppy Pics
• Preppy Shoes
• Preppy Girls
• Preppy Room Decor
• Preppy Shirts
• Preppy Profile Pictures
• Preppy Brands
• Preppy Makeup
• Preppy Images
• Preppy Sweatshirts
• Preppy Outfit Ideas
• How to Be Preppy
• Preppy Dresses

Where Can I Find High-Quality Preppy Wallpapers?

Preppy wallpapers can add a touch of classic charm to your devices. Here are top sources for finding these images:

Wallpapers.com

This site offers over 200 high-quality preppy aesthetic pictures for customizing:

• Desktops

• Mobile phones

• Tablets
  
  

Users can easily download these images for personal or creative use. In addition to aesthetic images, Wallpapers.com provides a collection of preppy profile pictures, allowing users to choose from 100+ options to enhance their social media presence.

Amazon

Amazon features a variety of preppy wall art and posters specifically designed for teen girls' rooms. These items include travel-themed prints and collage kits that can add a chic touch to any space. 

Etsy

Etsy is a great platform for finding unique, handmade, preppy pictures and decor. Many sellers offer customizable options that can fit personal styles and preferences. 

Unsplash

Unsplash provides free preppy images that can be used for commercial purposes without attribution. This source includes diverse photos featuring preppy fashion, accessories, and settings, making it an excellent resource for those seeking high-quality images.

Pinterest 

Pinterest offers a wide variety of preppy pictures and inspiration. Users can find countless images related to preppy fashion, room decor, and lifestyle aesthetics by searching for keywords like:

• Preppy style

• Preppy outfits

• Preppy room decor
  
  

Shutterstock 

Shutterstock is a great resource for finding preppy pictures, offering a vast collection of stock images that embody the preppy aesthetic. Here are some features and benefits of using Shutterstock for preppy-themed visuals:

Standout Celebrity Preppy Looks To Inspire Your Next Look

Beyoncé's Preppy Style Sets the Tone for 2024

Beyoncé kicked off the new 2024 year with the ultimate preppy look, proving she means business. The chic gray, black, and white plaid ensemble, composed of a tiny pleated miniskirt and matching blazer, looked like something straight out of a teenage character’s closet from a coming-of-age film. The Cuff It songstress opened her blazer to reveal a slightly sheer white plunging corset top and paired the look with matching strappy, pointed-toe stilettos. 

Beyoncé's NYE Accessories

Beyoncé further accessorized her sultry, sophisticated look with a small structured purse, white rectangle-framed shades, and—because it wouldn’t be NYE without some bling—a diamond necklace and statement drop earrings. 

Beyoncé's Glamorous Makeup and Nails

To show it’s all in the details, the singer included some close-up shots of her glam, which included shimmery silver eyeshadow to brighten up her inner corner and a glossy, muted pink lip. She also showcased her festively manicured nails, which featured a red Santa Claus hat design. As for hair, the mogul styled her platinum blonde locks in soft, voluminous waves.

Taylor Swift Leads the Preppy Charge

Taylor Swift also took a page out of the prep playbook this week. Following the cancellation of her Vienna Eras Tour show dates due to a foiled terrorist plot, Swift and her team are taking extra precautions before her London shows begin Thursday.

Swift Celebrates Eras Tour Wrap Party

That work has not stopped Swift from having a lighter moment with her team to celebrate their work on the European leg of the Eras Tour, which ends on August 20. DeuxMoi ran photos of Swift leaving her wrap party at the members-only club Annabel’s on Monday night. 

Swift's Preppy Plaid Outfit

Swift had a preppy moment sartorially, wearing 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.

Swift's Previous Plaid Look

Beauty-wise, she wore her hair down in loose waves and had on a red lip. You can see photos of her look here. This isn’t Swift’s first time in a plaid matching set. In December, she paired a Stella McCartney gold and black plaid jacket with a matching miniskirt and black top while out in New York City.

Related Reading

• Preppy Colors
• Preppy Girl Aesthetic
• Preppy Skin Care
• Pink Preppy
• Aesthetic Preppy
• Preppy Definition
• Preppy Nail Colors
• Preppy Braces Colors
• Preppy Hair Colors
• What Colors Are Preppy
• Preppy Room Colors
• Pink Preppy Wallpaper
• Preppy Meaning
• Preppy Wallpaper Laptop
• Hailey Bieber Hair
• Cute Nail Inspo

Try AI Personal Color Analysis for Free Today

The WhatColors app analyzes your skin tone to help you find your perfect colors. This fast and easy color analysis app gives you the perfect colors to wear based on your season. The app even breaks down your season based on your skin, eye, and hair color to give detailed results. Avoid colors that don’t flatter your unique complexion, and get personalized suggestions for nail colors! The free app is available on the App Store and Google Play. 

What Does WhatColors Tell You?

WhatColors gives you a detailed analysis of the colors that flatter your unique complexion. After you answer a few simple questions and upload a picture of yourself, the app analyzes your skin tone and determines your seasonal color palette. 

The app generates a list of colors that look great on you and even suggests shades to avoid. WhatColors also breaks down your results by type so that you can get color recommendations for:

• Outfits

• Accessories

• Beauty products like nail polish