Some people have it figured out when it comes to personal style. They have a go-to look that feels uniquely theirs and can effortlessly curate on-trend outfits that fit their aesthetic. Then, the rest of us need help with our personal style. There are many options, and the pressure to find a look that fits our personality and photograph well on social media can feel overwhelming. The preppy aesthetic is a classic style that is universally appealing, and who wouldn’t want to nail that? This blog will help you get started by exploring the many ‘preppy things’ that will help you elevate your personal style.

WhatColors’ AI personal color analysis app can help you master the preppy aesthetic. This unique tool will help you determine which colors look best on you to find the preppy things that fit your style. It will have you looking and feeling great in no time.

Table of Contents

• What are Preppy Things?

• Who Will Suit the Preppy Style?

• 42 Must-Have Preppy Things for a Preppy Wardrobe

• How Guys Are Doing Preppy Style, the 2024 Way

• Try AI Personal Color Analysis For Free Today

What are Preppy Things?

The preppy style is:

• Classic

• Understated

• Timeless

Preppy Elegance

The combination of sporty and sophisticated elements creates a polished appearance. The term preppy originated from preparatory schools and Ivy League universities in the Northeastern United States. 

It refers to the clothing worn by students attending these prestigious institutions. The preppy look exudes an air of elegance that never fails to impress. Achieving the preppy look is an excellent way to make a statement without going overboard.

The Enduring Appeal of Preppy Fashion

Preppy fashion has existed since the early 1900s and has always stayed in style. Crisp, clean lines and classic silhouettes remain popular today. The tailored look of preppy clothes references:

• A privileged lifestyle 

• A long-standing respect for tradition

What Do Preppy Things Look Like?

When it comes to fashion, preppy style typically involves items like boat shoes, polo shirts, and khaki pants. These are called:

• Preppy clothes 

• Preppy sweatshirts

Preppy outfits often utilize muted colors and sophisticated patterns like stripes or plaids. Accessories like scarves, hats, belts, and pocket squares add a traditional yet stylish feel to the look.

Where Do Preppy Things Come From?

As mentioned, the term preppy is short for preparatory. It references the clothing trends popular among students at New England prep schools in the early 20th century. The style became widely popular in the 1950s when teens in American culture adopted it. 

The look was characterized by the classic styles of the period, which the Ivy League schools heavily influenced. Today, the preppy aesthetic combines sporty and sophisticated elements that create a polished appearance.

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Who Will Suit the Preppy Style?

The preppy aesthetic is a style that prioritizes:

• Tradition

• Quality

• Polished appearance

With roots in the clothing worn by the Ivy League and elite private schools, preppy style evokes a classic, sophisticated look that never goes out of fashion. The preppy aesthetic is a versatile style that can be personalized to suit different tastes and preferences, making it suitable for various demographics.

Who Is Drawn to Preppy Style?

Preppy fashion appeals to those who value:

• Tradition

• Quality

• A polished appearance

The style is ideal for individuals who enjoy:

• Clean lines

• Classic colors

• Sophisticated yet casual look

Universal Style

From students and young professionals to fashion enthusiasts, anyone can rock the preppy aesthetic with:

• Personalized color palettes 

• Creative styling

The Classic Prep

The classic prep embodies timeless preppy style with its quintessential fashion staples. They love mixing and matching traditional pieces to create a cohesive look. Their wardrobe consists of:

• Crisp button-down shirts

• Tailored trousers

• Pleated skirts

• Classic trench coats

Classic Colors

When it comes to colors, the classic prep prefers a muted palette of:

• Navy

• White

• Beige

They accessorize with:

• Understated jewelry

• Leather watches

• Classic sunglasses

The Modern Prep

The modern prep mixes elements of preppy fashion with contemporary trends. They know how to update preppy staples:

• With unexpected accessories 

• Bold prints

Modern Twist

The modern prep isn’t afraid to experiment with:

• Bright colors

• Graphic tees

• Statement sneakers

• Funky jackets

They enjoy playing with texture and pattern, combining wool with silk or plaid with floral. The modern prep’s wardrobe is eclectic yet cohesive, with a dash of individuality that sets them apart.

The Sporty Prep

The sporty prep merges preppy fashion with athletic wear. They love to pair polo shirts with running shorts, zip-up jackets with yoga pants, and baseball hats with sneakers. They prefer breathable fabrics and stretchy materials that allow them to move freely. 

The sporty prep’s wardrobe includes activewear, tennis skirts, golf pants, and training shoes. Their accessories complete the look with the following:

• Sports watches

• Sweatbands

• Gym bags 

The Preppy Chic

Preppy chic is a fashion-forward style with a modern spin on preppy fashion. Preppy chic likes to mix preppy staples with high-end designer pieces to create a chic and sophisticated look. Preppy chic loves to experiment with:

• Bold colors

• Eccentric prints

• Edgy accessories

Modern Balance

They know how to balance preppy elements with modern trends to create a unique and refreshing look. Their wardrobe consists of:

• Tailored blazers

• Knee-length skirts

• Cashmere sweaters

• Designer loafers

The Preppy Rebel

The preppy rebel challenges traditional preppy fashion norms. They mix and match preppy items with punk rock or grunge-inspired accessories. The preppy rebel adds their unique style to preppy staples by wearing:

• Distressed denim

• Leather jackets

• Statement boots

• Skull jewelry

Their wardrobe is a mix of vintage and modern pieces, with a dash of attitude that sets them apart.

Unlock Your Colors and Transform Your Style

WhatColors helps you find what colors to wear based on your skin tone. Thanks to our patented color match technology, you can 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 color 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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42 Must-Have Preppy Things for a Preppy Wardrobe

The preppy aesthetic has evolved but remains one of today's most popular styles. The look is polished, cheerful, and colorful, inspired by classic New England styles. You can achieve it by combining:

• Bright hues

• Pastel tones

• Classic prints, like plaid, gingham, and argyle

The preppy aesthetic is also closely related to a privileged lifestyle, often seen in depictions of the elite in film and television. As a result, the style evokes a mood of affluence and sophistication, even if you’re shopping on a budget. If you love the look, here’s a comprehensive list of 42 trendy items to help you achieve the preppy aesthetic in 2024.

Preppy Home Decor

1. 6 Pcs Preppy Throw Pillow

Preppy home decor is a thoughtful gift for your friends. This pillow is designed for naps and decorating in the bedroom or sofa. The soft fabric and convenient zipper make it hassle-free to use or wash them.

2. 110 Pcs Preppy Wall Decor

Amaze your recipients with stickers to decorate the room in a preppy style. One hundred ten details with different sizes and textures will challenge the user's creativity. Send this unique and thoughtful gift to your hot pink enthusiast.

3. Preppy Room Decor

The frameless pink room painting posters are creative gift choices for home decoration. The poster is made of heavy-duty card material and coated with a PET film layer to ensure long-term use.

4. 6 PCS Pink Preppy Room Decor

If you are invited to a girl's birthday or a slumber party, do not hesitate to choose the 6 PCS pink preppy room decor as a unique gift. Preppy-themed ornaments are classic and modern, helpful in:

• Giving a new look to a space 

• Expressing personal style

Preppy Stationery

5. Preppy Journal

If you are seeking a gift for someone who loves a preppy aesthetic, this journal is your choice. The look ultimately got the recipient's heart with:

• The familiar pink textured cardboard 

• A familiar smiley face

6. Spiral Lined Notebook

A custom-designed colorful pineapple notebook is a lovely gift for a preppy friend on a weekend date. The 118-page lined notebook is a valuable assistant for daily study. The details of the letters monogrammed on the cover will be the highlight to excite users.

7. Trendy Preppy Y2k Notebook

Shape your style by adding trendy preppy Y2k notebooks now. The 118-lined page notebook is helpful for:

• Study 

• Daily purposes

This is a unique preppy gift printed on the front cover with a personalized design.

Preppy Clothing

8. Smile Embroidered Sweatshirt 

Send love and care to your friends and family with a smile-embroidered sweatshirt. The tie-dyed sweatshirt has patchy colors, and the face on the left chest is outstanding. This gift will help girls have more new outfits.

9. Have a Good Day Sweatshirt

Give your preppy friends or sisters a sporty hoodie on a birthday or anniversary and witness their surprise. The basic designed hoodie with the message printed on the back will become the wearer's favorite item.

10. Preppy Crew Neck Sweatshirt

Dynamic yet elegant, Preppy Crew Neck Sweatshirt is a delicate gift for collegiate girls. The oversized crew neck sweater highlighted with the pink skeleton design is a unique gift for the graduation of preppy-style girls.

Preppy Accessories

11. Preppy Bracelets Stack

The preppy bracelet stack is a unique summer gift idea for energetic girls. Inspired by the preppy starburst, this vibrantly colored bracelet with a smiley face or star in the center is truly a piece of jewelry every girl should have.

12. Custom Chain Necklace

Order a custom chain necklace as a meaningful gift for an elegant girl in summer or the new school year. A necklace with many links creates a lovely look for ladies, while a personalized pendant with a name's initials makes it unanimous.

13. Preppy Heishi Bracelets

Transform your style and versatility with preppy heishi bracelets. The order contains 16 bracelets of different colors and materials, giving you countless options for other occasions. No girl can say NO to this lovely gift.

Decorative Preppy Items

14. Sound Wave Preppy Wall Art

More than wall art, this is a creative preppy present for birthday parties or housewarming parties. The sound wave is created from the recipient's favorite song and singer. It can carry a secret message you want to convey.

15. Cute Preppy Tapestry for Bedroom

Turn the space into a sweet paradise with a cute preppy tapestry for the bedroom. The smiley face rug is the right size and color. You can hang it on many different sites in the house. This is a gift that every girl would gladly have.

Preppy Gifts For Girls

16. Personalized Baby Duffle Bag

Are you looking for a meaningful gift for your baby girl? A personalized baby duffle bag is an option. The soft cotton seersucker fabric has monogrammed letters, making it a handy and fashionable item for children.

17. Preppy Pink Gingham Tea Set

Baby girl needs a tea set with dolls or friends, and a preppy pink gingham tea set is your perfect gift. The set consists of:

• A teapot with a lid

• A sugar bowl with a lid

• 4 tea cups

• A rectangular serving plate and tray for fun tea time.

18. Preppy Watercolor Pouch

Every girl needs a valuable, cute accessory, like a preppy watercolor pouch. Pink hearts are sharply printed on 100% polyester to give a great form and delicate appearance. Available sizes make it easy to choose the perfect gift for your girl.

19. 6 Cute Preppy Coasters

The place where the water cup is kept must be decorated to match the car owner's style. The receiver had never seen cuter car coasters than these. A lover of preppy fashion will fall in love with this vintage present.

20. Smiley Paper Plates

Bring the party to life with smiley paper plates. A party table with these cute pastel smiley face plates will leave an unforgettable impression. Give this lovely gift to those with a birthday or graduation party.

21. Preppy Cosmetic Bag

Show your care by sending her a preppy cosmetic bag. It is made of high-quality PU material, and its compact size ensures long-term use. Every girl will be happy with this sweet gift.

22. Personalized Smiley Face Preppy Tumbler Cup

You can gift a beautiful girl by skipping the personalized preppy tumbler cup. The funky mug with the recipient's name will become a handy and adorable addition for her daily use.

Preppy Gear For School

23. Tennis Racket Notepad 

Why not have a notepad of your own? The tennis racket details and water-printed decoration give it a realistic style. The best part is that the recipient's name is printed on it. This is a beautiful gift for busy people to carry with them.

24. Monogrammed Short Sleeve Pocket T-Shirt

Sparkle summer with a monogrammed short-sleeve pocket T-shirt. This item is designed in a variety of bright colors. The pocket will be personalized with letters that abbreviate the recipient's name or have special meanings.

Preppy Clothing For Sports

25. Flowy Workout Shorts

Flowy workout shorts are a must-have for any woman in sports activities. These shorts are soft and comfortable, helping women:

• Feel confident 

• Move more quickly

This is an excellent gift for the preppy who loves sports.

26. Preppy Smiley Face Friendship Bracelets

Celebrate friendships with unique smiley face preppy bracelets. Two bracelets are hand-knitted with cotton thread accents. The item has a smiley face motif. This boho and hippie gift is a testament to sisterhood.

Preppy Home Textiles

27. Indian Pink Bedspreads

Indian pink bedspreads add a sense of elegance to the bed. Two layers of cotton are quilted with red thread Kantha stitches. The crisp block print and pink color create a creative, preppy home decor gift.

28. 6 PCS Pink Preppy Room Decor

If you are invited to a girl's birthday or a slumber party, do not hesitate to choose the 6 PCS pink preppy room decor as a unique gift. Preppy-themed ornaments are classic and modern, helpful in:

• Giving a space a new look 

• Expressing personal style

Preppy Fashion Accessories

29. Kate Spade Heart of Gold Bangle

Preps could always use another gold bangle, and this best-seller from Kate Spade is a cut above the usual ones. It’s inscribed with the heart of gold as a reminder of how much you love them.

30. Mejuri Bold Pearl-Drop Earrings

Pearls have long been associated with preppy style, meaning that your giftee probably has a strand or two sitting around—perfect for pairing with these delicate gold-and-pearl earrings from internet-beloved brand Mejuri.

31. Lele Sadoughi Bardot Ribbon Headband

Is any outfit that couldn’t benefit from a velvet headband bedecked with the most perfect bow? We think not.

32. Mark & Graham Small Cabana Stripe Travel Jewelry Case

Add a monogram—this eye-catching jewelry case has eight style font options for your jet-setting best friend. After all, you can never go wrong with a personalized gift.

Preppy Clothing Staples

33. The Classic Oxford Shirt

The classic Oxford shirt is one of the most timeless pieces in preppy fashion. The button-down shirt is a staple for every preppy wardrobe. The traditional Oxford shirt comes in a solid light blue or white color. The shirts have evolved over time, and you can now find them in different:

• Colors

• Patterns

• Sizes

An Oxford shirt is versatile and can be worn in any season, whether layered or alone.

34. The Cable Knit Sweater

The preppy style is all about simplicity, and you can achieve that with a cable knit sweater. The sweater is:

• Cozy

• Comfortable

• Stylish

It’s a staple piece that can be dressed up or down, making it a valuable item in preppy fashion. The sweater is often made of wool, but it can be found in different fabrics, including cashmere. It comes in neutral colors such as beige or navy, but you can also find it in bright colors like pink.

35. The Chino Pant

It’s impossible to talk about preppy fashion without mentioning the Chino pants. They are a staple in every preppy wardrobe and for good reasons. They are versatile, comfortable, and can be worn with any style. 

Chinos were initially meant for the military but evolved into a popular preppy style. They come in different colors, such as khaki, navy, and beige, and you can style them with a:

• Button-down shirt

• Bolo shirt

• Sweater

36. The Polo Shirt

The polo shirt is another classic preppy piece. Invented by Rene Lacoste in the 1920s for tennis players, it has evolved to become a must-have in every preppy wardrobe. 

The polo shirt is versatile and can be worn to various events, be it a golf game or a picnic. It comes in multiple colors, patterns, and styles, so you’re guaranteed to find one that suits your needs.

Preppy Shoes

37. The Preppy Loafers

Finally, we end with one of the most important preppy pieces: loafers. These shoes are:

• Comfortable

• Stylish

• Perfect for your preppy style

Loafers were first invented for men, but now you can find them in different styles and colors for women. They go well with chinos, shorts, or even jeans, and they are perfect for a casual or dressy occasion.

38. Boat Shoes

Boat shoes are an essential addition to any preppy wardrobe. They provide comfort and add a touch of nautical charm to any outfit. Look for classic styles in neutral colors like brown or navy blue that can be easily paired with different outfits.

Preppy Accessories

39. Classic Leather Bag

A classic leather bag is a timeless preppy accessory that oozes sophistication. Whether you choose a satchel or a tote, this accessory is functional and stylish—perfect for carrying all your essentials throughout the day. Look for tan, brown, or navy blue for a traditional preppy vibe.

40. Printed Scarves

Throwing on an intricately printed scarf is a surefire way to add dimension and personality to a preppy outfit. Choose scarves with designs like polka dots or stripes to achieve a classic preppy look. 

You can also use a scarf to diversify your outfit by tying it on your handbag or around your neck for a chic Parisian flair.

41. Classic Sunglasses

To round out your look, nothing says preppy quite like a classic pair of sunglasses. Choose a wayfarer or aviator style with either brown or black lenses for a hint of sophistication. Not only do sunglasses make a fashion statement, but they also protect your eyes from harmful UV rays.

42. Printed Scarves

Throwing on an intricately printed scarf is a surefire way to add dimension and personality to a preppy outfit. Choose scarves with designs like polka dots or stripes to achieve a classic preppy look. 

You can also use a scarf to diversify your outfit by tying it on your handbag or around your neck for a chic Parisian flair.

How Guys Are Doing Preppy Style, the 2024 Way

In 2024, the preppy aesthetic returns with a fresh, modern twist. Current preppy trends are all about relaxed fits and unexpected pairings. Tailored shorts are worn with casual tees instead of traditional button-downs. Argyle patterns are being mixed with streetwear elements. Even the iconic polo is getting a refresh—cut in a boxy silhouette and styled with baggy jeans instead of khakis.

Old Money Aesthetic 2.0

The old-money aesthetic is the preppy revival’s cooler, more approachable cousin. It’s still aspirational but less about wealth and status, and more about:

• Individuality 

• Style

TikTok’s take on the aesthetic has unearthed a treasure trove of vintage looks from the 90s and early 2000s that evoke the charm of wealth without the stuffiness. Think less Gossip Girl and more Royal Tenenbaums.

The Return of Preppy Fashion

Preppy fashion, of course, is a familiar invention. Before it was a trend, it was a lifestyle–the dress code of American and English elites stretching back to the early 1900s. They sent their kids to preparatory schools—that’s where the term preppy comes from—before college; they played lacrosse, attended society debuts, and used holiday more often as a verb than a noun. 

It wasn’t until 1982 when Lisa Birnbach published her seminal satire The Official Preppy Handbook, that prep went mainstream. Suddenly, everyone was in seersucker suits and rugby shirts. Labels like Brooks Brothers, Lacoste, and J. Crew dug their way out of university campuses and wriggled into the everyman’s closet.

Preppy Fashion’s New Look

The popularity of prep has waxed and waned since its ’80s heyday, but it never returns looking the same. Sure, there are the base pieces—the polos mentioned above, Oxford shirts, and Sperry Top-Siders—but they’re worn with another goal: an alternative mood. 

“When I redesigned prep in 1985,” New York’s Tommy Hilfiger told WWD, “it was disruptive due to the introduction of oversized, relaxed silhouettes, a stark contrast to the structured preppy look of the time. Each decade has its unique take on prep style.” In the mid-2000s, Gossip Girl proffered that take, stuffed with 30-year-old-looking 16-year-olds in ties and waistcoats.

The Preppy Revival: 2024 Edition

But how are we styling preppy pieces now, in the year 2024? Jeremy Molcanovs, menswear buyer at Incu, tells GQ that the newest wave of prep has an element of irony. “I’ve always viewed preppy style as this contradictory blend of playfulness and pretentiousness,” he explains, “but that stuffy country club vibe is cooling off, or it’s intentionally being worn ironically now. The new context is still playful, but its perfection has been dropped, and its mix-and-match nature has been embraced.”

Modern Preppy

As opposed to previous waves, or even the earlier iteration of old money style that dominated 2023, preppy style moving forward, observes Molcanovs, is keen to shake off, or at least challenge, its history of privilege and exclusivity. “It’s less conservative and without the antiquated rules that come with particular movements in menswear,” says Molcanovs. 

“There is more focus on individuality, rather than if the sleeve of your suit jacket hits your wrist bone. Silhouettes are looser, and it’s a bit more rough around the edges—more punk, less Ivy League.”

What to Wear for Preppy Style 2024

Molcanovs says that the preppy style he’s been seeing of late borrows from both casual tailoring and workwear and names Nakada Shinsuke, creative director of the preppy, Americana-inspired Japanese label Beams Plus, as his favorite poster boy of the trend. (Gossip Girl’s Chuck Bass, he admits, isn’t a flawed model either.) 

Charles Jeffrey Loverboy, Steven Stokey Daley, and Grace Wales Bonner are among the designers reinterpreting prep’s traditional codes with their own bent—shrunken knits, metallic schoolboy shorts, hyper-feminine cardigans—and styling those pieces with more laidback, streetwear-inspired accessories.

Key Pieces to Achieve a Neo-Prep Wardrobe

As for the items you’ll need to build your neo-prep wardrobe? The humble necktie is a great place to start. “It’s nice to pair that back with a simple zip jacket rather than a crested blazer,” advises Molcanovs, “which might not be everyone’s cup of tea. Rugby shirts are an easy option if you want to embrace the look with a piece that is super versatile.”

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Try AI Personal Color Analysis For Free Today

WhatColors helps you find what colors to wear based on your skin tone. Our patented color-match technology enables you to get your season's perfect colors. Avoid colors that are a definite no. Based on your skin, eye, and hair color, find the ideal 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.