As the summer sun fades and crisp air rolls in, we encounter the same challenge: transitioning our wardrobes from summer to fall. With so many options, it can be overwhelming to determine what styles, fabrics, and colors to focus on for the upcoming season. If you’re looking for a classic and timeless aesthetic that will make curating your fall outfits a breeze, the preppy aesthetic is a fantastic choice. This blog provides tips and tricks for mastering the preppy aesthetic and incorporating it into your wardrobe to elevate your style this fall.

WhatColors’ AI personal color analysis app can help you implement these ideas to achieve your goals. By analyzing your unique skin tones and undertones, the app generates a personalized palette of colors that will complement your natural features to help you look and feel your best.

Table of Contents

• What is Preppy Aesthetic?

• Who Is the Preppy Aesthetic Most Suitable For?

• 13 Key Elements of the Preppy Aesthetic Style

• Related Aesthetics within Preppy

• 23 Timeless Preppy Aesthetic Outfit Ideas and Style Tips

• 8 Do’s and Don’ts of the Preppy Aesthetic

• How to Look Like a Preppy Girl?

• What Is Gen Z & Gen Alpha Preppy?

• 3 Major Keys to the Modern Preppy Look

• 15 Best Preppy Wardrobe Items to Shop in 2024

• 51 Key Influential Preppy Aesthetic Brands

• Try AI Personal Color Analysis For Free Today

What is Preppy Aesthetic?

The preppy aesthetic is one of the most recognizable styles that evoke a distinct image and vibe. Preppy has become synonymous with the following:

• Affluent

• The elite

• The upper crust of society
  
  

People who embrace the preppy style exude sophistication, class, and wealth.  Yet, in practice, the preppy aesthetic is much less about money and status and more about tradition, heritage, and classic style that transcends time and trends.

Preppy Aesthetic History

Preppy fashion originated in the early 1900s when students in Ivy League universities developed a distinct style reflecting their:

• Privileged backgrounds 

• Academic pursuits
  
  

It wasn’t until the 1950s and 60s that the preppy look gained widespread recognition due to iconic figures such as Princess Diana. The Official Preppy Handbook, published in the 1980s by Lisa Birnbach, further popularized this style by highlighting its key components, including:

• Polo shirts

• Navy blazers

• Boat shoes
  
  

In recent years, the character of Blair Waldorf in the television show Gossip Girl has pushed the resurgence of the preppy aesthetic even more. Her polished outfits, characterized by impeccably tailored blazers, pleated skirts, and sophisticated accessories, perfectly capture the essence of preppy fashion.

Who Is the Preppy Aesthetic Most Suitable For?

The preppy aesthetic revolves around timeless looks. If you carefully examine a preppy outfit, you won't find much in the way of trendy pieces. Instead, you'll find many classic, sophisticated styles that have been popular for decades. If you want an outfit that will never go out of style, you should look for pieces that fit the preppy definition. 

You can always add flair and make them unique to your style. But the overall look will be elegant and polished, never flashy or gaudy.

Am I Preppy?

You Love the Classic Look

Do you prefer styles that stand the test of time over fashion trends? The preppy style perfectly matches you because timeless pieces characterize preppy outfits.

You Have an Old-Money Lifestyle

If you love furnishing your home with elegant home decor and spending Sundays talking about your favorite tennis players, the preppy style will fit your old-money lifestyle!

You Love Neutral Colors

The preppy style is excellent if your primary color palette is:

• Black

• White

• Navy blue

• Grey

• Other light colors
  
  

These are the colors associated with American collegiate charm.

You Are Not Into Fast Fashion

Do you avoid buying from fast fashion brands that follow fleeting trends? If so, the preppy style is definitely for you. Preppy fashion is all about quality and timeless style. True preps only buy clothes that are made to last, not only in quality but in style.

13 Key Elements of the Preppy Aesthetic Style

The preppy style is characterized by a classic, timeless aesthetic that never truly goes out of style. As a result, I’ll bet you already have some pieces that define your wardrobe's look. To get you started mastering the preppy aesthetic, here are fundamental elements of preppy style, encompassing essential garments, prevalent patterns and colors, and styling techniques suitable for both men and women:

1. Knit Tops

A knit top can instantly give your outfit a preppy style. Whether a pullover, a uni sweatshirt, a cardigan, or a vest, wearing a striped, patterned, or solid-colored knitted top will give you that preppy vibe. Make your outfit even more collegiate, but wearing your knit top over a button-down shirt with your collar popped out.

2. Plaid and Argyle

You can’t go wrong with plaid and argyle patterns when it comes to preppy aesthetics. The checked stripes and diamond patterns instantly evoke a preppy flair. Plaid and argyle can come in virtually any color. Go for pastels in the spring and summer and darker jewel tones for the fall and winter seasons. 

Argyle vests and plaid pleated skirts are especially synonymous with preppy outfits. Channel your favorite high school or college television show characters for the quintessential preppy outfit.

3. Statement Collar

A statement collar may seem unexpected, but it’s one design element that can instantly inject a little preppy style into your outfit. Whether it be a rounded Peter Pan collar, a ruffled collar, a pointed Chelsea collar, or an oversized style, a top or a dress with an eye-catching collar is all you need for an easy preppy outfit.

4. Pleated skirts and dresses

No academia look is complete without a pleated skirt. Make it a plaid pleated skirt, and you’ll take the preppy style to another level. Ace the private schoolgirl look with a plaid pleated miniskirt paired with a knitted vest and a blazer worn over a classic collared button-down top. An alternative to the pleated skirt is a full-on pleated dress featuring a collared neckline.

Whichever you prefer to wear, either preppy outfit will have you looking like you’re ready for your next class.

5. Mary Jane’s and Loafers

When it comes to preppy kicks, nothing says school girl quite like classic loafers and Mary Jane shoes. Whether you prefer the shoe styles as flats, with heels, or with high platforms, stepping into Mary Janes or Loafers will have you giving every preppy school girl a run for their money. Just don’t forget to wear socks, especially knee-high versions, for the full preppy effect.

6. Headbands, Berets, Bows, and Socks

The devil is in the details, and small accessories can make a big difference in your overall look when it comes to the preppy aesthetic. A ladylike headband or a chic beret can easily complete your preppy outfit. You can also opt for a girly bow clipped to your hair or ribbon tied on your top. 

Slipping into socks, especially patterned, ruffled, or knee-high styles, will have you walking, not just with an extra pep but with an extra prep.

7. Oxford Button-Down Shirts

Nothing quite says preppy like the classic oxford shirt, especially one from Polo Ralph Lauren.
The Oxford button-down shirt is a quintessential component of the preppy wardrobe. Known for their soft, woven fabric and button-down collars, these shirts embody relaxed sophistication.

They can be paired with blazers and sweaters or worn alone, making them a versatile choice for any preppy ensemble.

8. Navy Blazers & Tweed Jackets

Make a polished preppy statement in a double-breasted navy blazer with gold buttons.
The navy blazer, often adorned with gold buttons, is an iconic piece in preppy style, symbolizing a blend of:

• Nautical charm 

• Academic refinement
  
  

On the other hand, tweed jackets, inspired by the British preppy style, project an image of relaxed formality while adding texture to the outfit.

9. Chinos

Chinos, originally military wear, have found a place in the preppy wardrobe due to their versatility. They balance formal trousers and casual denim, making them a staple in creating smart-casual ensembles.

Traditional preppy style often favors chinos in earthy tones like:

• Beige

• Khaki

• Navy
  
  

10. Sweaters

Sweaters, particularly those with a cable-knit design, are integral to the preppy aesthetic. They add a layer of warmth and sophistication to any ensemble and can be effortlessly draped over shoulders for an additional dash of preppy charm.

11. Loafers

Loafers, in penny or tassel style, are the footwear of choice in preppy style. Known for their slip-on design and sleek look, loafers complement casual and formal preppy outfits.

They are typically made of leather or suede and can be worn with or without socks, depending on the:

• Occasion 

• Season
  
  

12. Ties

Preppy style takes a playful approach to ties, with prints ranging from classic stripes to whimsical motifs. Repp ties, characterized by their ribbed texture and diagonal stripes, are a popular choice in preppy style.

13. Accessories

The preppy style embraces accessories as an opportunity to add personal flair to an ensemble. Essential preppy accessories include:

• Cufflinks

• Scarves

• Watches

• Belts
  
  

Discover Your Colors

WhatColors helps you find what colors to wear based on your skin tone. Finally, get your season based on our skin tone, thanks to 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.

Related Reading

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

Related Aesthetics within Preppy

The Ivy Aesthetic: A Classic Look With Serious Academic Vibes

The Ivy aesthetic draws inspiration from college students' preppy clothing from the 1940s to the 1960s. This look is heavily associated with Ivy League schools, and as a result, it gives off serious academic vibes. Ivy's style can be recognized by its:

• Vintage appeal 

• Muted color palettes
  
  

Think wool sweaters, cardigans, and blazers paired with collared shirts, neckties, or bows. The bottoms are often chinos or classic plaid skirts. Ivy looks may also incorporate:

• Argyle patterns 

• Pairs of loafers or oxfords
  
  

Trad Style: The Grown-Up Version of Ivy 

Trad style, short for traditional, is the grown-up extension of Ivy. It is more noticeably vintage than preppy and evokes the look of outfits worn by the upper crust in the early to mid-20th century. Bright colors, such as socks, are usually only used for a single accent piece. 

Suits are tweed, Prince of Wales check (usually gray), or navy pinstripe. Blazers can be double-breasted or single-breasted. Elbow patches on tweed jackets are common. This is recognized by the pairing of loafers with a two- or three-piece suit.

Neo Prep: A Modern Take on Preppy Style

Neo Prep, or Nouveau Prep, is a more modern take on the preppy aesthetic. It incorporates elements of street style and is more casual than traditional preppy looks. Neo prep adds sneakers, jeans (sometimes cuffed at the ankles), and baseball caps to outfits that include blazers. 

Argyle is a common pattern for socks. Facial hair, such as beards and mustaches, is worn by men. The Tommy Hilfiger designs are from the 2000s, and most outfits Kiel James and Sarah Patrick wear are Neo Prep.

Southern Belle Style: A More Feminine Approach to Southern Prep

The book and movie Gone with the Wind heavily influence Southern Belle style. The Southern Belle aesthetic values:

• Tradition

• Family

• Politeness

• Femininity
  
  

It is controversial due to the historical association with slavery and modern associations with racism and the Confederacy. Plantation Weddings are common for Southern couples.

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

23 Timeless Preppy Aesthetic Outfit Ideas and Style Tips

So, what exactly constitutes preppy style? No longer just a blend of polo shirts and khakis, the preppy aesthetic now combines classic elements with:

• Vintage

• Nautical

• Goth influences
  
  

Outfits are crisp and colorful, often giving off an old-money vibe. 

Instead of looking like you just walked off the yacht, modern preppy outfits incorporate casual, street, and grunge-style elements for approachable looks that won’t break the bank. The following 23 items will help you nail the trend this fall.

1. Proud Monograms

Your average pullover sweatshirt is transformed into a varsity look with one letter — collegiate font patches are the ultimate preppy accessory.

2. Cher Horowitz-Inspired Plaid

Do Cher proud in a yellow mini straight out of the movie Clueless. Style it up with a graphic knit to bring this '90s favorite into 2022.

3. Vintage-y Cable Knit

The combo of a red cable knit sweater and jeans is an easy, preppy outfit to pull off. Grunge down the look with Docs and a trendy shoulder bag.

4. Cool in Crimson

Layer a crisp white button-down under a logo t-shirt and add a pop of color with cherry red accessories. Preppy fashion never looked so cool.

5. Trouser Shorts

When temps get too high for full-on wool trousers, take notes from Barbie Ferreira, who styled long plaid shorts with a super relaxed button-down and choker for an updated prep look.

6. Sweater (Vest) Weather

Layering a sweater vest over a preppy button-down is perfect for days when you want to get away with wearing leggings while still looking like fashion.

7. Preppy Prints Turned Cozy

Trousers aren't just for internships and interviews — they'll pair perfectly with your fluffiest, coziest cardigan, balancing out the look for a laid-back, preppy vibe.

8. Plaid on Plaid

Don't be afraid to wear a monochrome look with prints. Hailey Bieber knows that plaid is practically neutral when it's in classic shades like:

• Grey

• Black

• White
  
  

9. Belts, Caps, and Bags

The accessories can make or break your preppy outfit. Classic bags, leather belts (for pants or dresses, ofc), and cabby hats will take any ensemble to the next level.

10. Gothic Peacoat

This outfit proves that preppy style can take on any vibe – even Victorian goth. Pair up preppy items, like a peacoat you'll wear for years, with edgy details, like these leather over-the-knee boots.

11. Varsity Jacket

Sift through your local thrift store (or raid your dad's closet) for a retro letterman jacket that gives off all the preppy feels. Pair with a vintage-y concert tee and pants.

12. Nautical Cardigan

This is the ultimate preppy outfit. An oversized stripe-trim cardigan adds effortless elegance to a white tee and jeans. Keep accessories low-key so the sweater steals the show.

13. Clean White Turtleneck

A fitted white turtleneck is a tried and true preppy favorite. You can layer under your favorite sweater, tuck it into high-waisted jeans, or double down on preppy vibes with a nautical striped skirt.

14. Updated Penny Loafers

Make your classic penny loafers feel fashion-y with cropped jeans and cute striped socks — any outfit instantly becomes preppy when you add a pair of black slip-on loafers.

15. A Classic Varsity Sweater

Nothing says preppy like a classic Lacoste varsity knit. Wear your oversized with slim joggers, or dress it up with a slim trouser and boots.

16. Wool Pants + Stripe Button-Up Shirt + Cashmere Crewneck + Sandals + Handbag + Sunglasses

Start off with these Italian wool pants, perfect for still keeping yourself somewhat warm while showing off the beautifully tailored look of the trousers. There is nothing quite like a good striped, crisp button-down shirt for your top to welcome the warmer weather. This versatile piece can easily transition from the office to your weekend brunch – all it takes is a little styling! 

For this look, tuck in your shirt and roll your sleeves. Open up a few buttons for a more relaxed, laid-back look that screams preppy. Tie this beautiful beige cashmere sweater over your chest for an elegant way to stay warmer and prepared for when the wind hits. Accessories are crucial for the final look's full potential. Add:

• An oversized pair of brown sunglasses

• A structured crossbody bag

• A pair of summer-ready, elegant sandals
  
  

17. Miniskirt + T-Shirt + Collared Sweater + Shoulder Bag + Gold Watch + Loafer + Socks

Trendy and classy do get to go together sometimes! This preppy outfit combines timeless pieces with a more modern styling approach, combining these two elements into one cute look. Begin with this knitted miniskirt, one of the most popular pieces in the preppy aesthetic!

Chic Layering

On top, a simple white tee will do the trick, keeping things sleek and simple. For a subtle but charming pop of color, layer this organic cotton collared sweater over your shirt. Not only does the collar detail tie back into the aesthetic we’re aiming for, but the silhouette of the sweater also beautifully complements the shorter proportions of the skirt. 

Again, accessories are a must here as they emphasize the outfit's mood and bring it all together. A simple and chic black handbag and a black pair of loafers tie in with the skirt and balance out the look's color palette.

18.Sweater Vest + Poplin Shirt + Wide-Leg Wool Pants + Pumps + Hoop Earrings

Making for a less trendy take on the preppy aesthetic, this outfit still finds a way to integrate more contemporary aspects into this otherwise classic look seamlessly. These wide-leg pants make a statement with their gorgeous shade of brown and subtle plaid pattern, bringing depth and interesting proportions to the look. While plaid mini skirts tend to be a common way of seeing this pattern in classic preppy style, finding them in other pieces like trousers is a great way to diversify your collection!

Top Layer

A basic button-up collared shirt is the perfect pair, bringing a more traditional element into the mix. On top of your shirt, layer this checkered-stitched sweater vest. The pattern on this piece speaks to the plaid pattern on the pants, tying both pieces together efficiently but subtly, which is not too overpowering either. Bring out the collar of your shirt on top of your sweater, and roll up the sleeves slightly for a casual styling touch that elevates the entire look. 

For shoes, these kitten heel pointed pumps play into the timeless and classic feel of this ensemble while also adding some texture and a little extra flair with its chic design. As for accessories, leave the focus to the clothes and opt for an understated pair of bubble hoop earrings to bring it all together.

19. Lady Jacket + Elbow-Sleeve T-Shirt + Straight Jeans + Ballet Flats + Watch

Lady jackets have my heart, and they belong within the preppy aesthetic category, too. From quickly dressing up a pair of jeans and a white tee to being the focus of an entire outfit, this piece is versatile in the best ways – and truly perfect for styling year-round! More structured and polished than a knit cardigan, lady jackets allow you to add structure and poise to the most basic of looks, regardless of the season. That’s exactly what we’re going for here!

French Preppy

This preppy look can also be considered French-inspired by many, as it uses a lot of elements that I love about French fashion. Take a break from your skinny jeans and experiment with a different denim fit by starting this look with these 90s straight jeans. This straight silhouette makes for just the right fit for a timeless and elegant pair of jeans – not too tight and loose! On top, an elbow-sleeve t-shirt does the trick, offering slightly more coverage to keep you:

• Comfortable 

• Warm 
  
  

Layer your navy lady jacket on top, instantly adding that preppy charm to your ensemble. Opt for a delicate gold watch as your main accessory, elevating your outfit with a more polished flair. As for shoes, these ballet flats will slip onto your feet easily, complementing both your look and your levels of comfort throughout the day.

20. Linen Shorts + Polo Cardigan Sweater + Mary Jane Flats + Cat-Eye Sunglasses + Tote

Yes, the preppy aesthetic can be confusing and lead to many misconceptions from those who aren’t super familiar with the style – one of the main ones being that there is no such thing as a casual preppy outfit. While this is not true, this outfit officially disproves this theory and shows you exactly how this simple look falls under the preppy aesthetic.

 More than just specific types of outfits or clothing pieces, the preppy aesthetic is about using classic styles and silhouettes for elegant overall ensembles. While these looks can include many accessories, simplicity is also a way to be successful when finding the perfect preppy look. For this look, we are starting with a pull-on linen short; this super easy-to-wear, breathable fabric lays the casual foundation of the look.
 

Polo Cardigan

On top, pair your shorts with this ribbed polo cardigan sweater. This piece's slouchy fit matches the shorts' fit, while also elevating the look with features like a collar and a striped pattern. Especially when it comes to putting together a stylish look filled with preppy clothes, relying on classic patterns is the best way to bring some variety to your collection while still keeping things neutral and timeless. 

This look again proves that simple doesn’t have to mean boring for accessories. This tote keeps your belongings safe while adding some structure to this relaxed ensemble. Mary Jane shoes add another classic element to the look, finishing off a sleek preppy combination.

21. Pleated Linen Short + Button-Down Shirt + Leather Belt + Cashmere Sweater + Ballet Flat + Tote Bag

While bright colors can be visually appealing, neutral tones are preferred. Also ideal for spring, this next outfit is a dream for anybody who loves classic neutral shades – and a pop of light blue. These pleated linen shorts kick off the look. Shorts can often feel too casual if you are not used to styling them within this aesthetic, but there are many ways around this obstacle when it comes to crafting truly classic looks during the warmer months of the year. 

Luxurious Fabrics

Opting for fabrics like linen instantly adds a luxurious texture to your look, setting the tone for the outfit and balancing the more casual design of the shorts as well. On top, this blue button-down shirt continues to dress up the bottoms. Style your shirt by rolling up the sleeves and tucking it into your shorts for a better fit and overall look. 

Cashmere Versatility

Whether you wear your cashmere sweater tied draped over your shoulders, keep it inside my tote, or have it on, this piece can be integrated into this look a number of different chic ways. Bringing another classic tone into the neutral color palette of the outfit, this sweater adds a beautiful extra layer. 

This large tote bag matches the soft beige tone of the linen shorts, making for a cohesive and thought-out outfit that fits perfectly into the preppy aesthetic. A deeper brown shade makes for the perfect accessories – a skinny belt and a pair of beautiful ballet flats finish off this ensemble.

22. Chino Shorts + Button-Up Shirt + Shoulder Tote + Slip-On Sneaker + Stud Earrings

Hot weather shouldn’t get in the way of your style, and this next look shows you exactly how that can be done. These chino shorts keep you cool while still very much giving off the preppy aesthetic with their cut and structure. In this beautiful navy color, this piece also features a higher rise and an elegant tailored look. 

Breezy Button-Up

Button-down shirts are an absolute staple item for any preppy wardrobe, but sometimes, the temperatures might get in the way. This bib button-up shirt keeps the look you love in this far cooler, more breathable short-sleeve version. Made from a herringbone twill fabric, this shirt still elevates your look through its materials and silhouette while definitely not compromising on your comfort. 

Accessorize to Perfection

Add a touch of sparkle with these cubic zirconia studs, polishing your look even more. As for accessories, opt for this classic beige tote and a pair of comfortable white sneakers. The more casual shoe choice helps us to balance out the more elegant clothing pieces and keeps you comfortable throughout the day as you relax or run your errands for the week.

23. Wide-Leg Jean + Button-Up Shirt + Ballet Flat + Leather Tote + Leather Strap Watch

For true lovers of the preppy aesthetic, this next look can certainly be found in your closet! Starting with these slim wide-leg jeans, this look once again relies on truly classic wardrobe staples and mindful accessories for the real preppy effect. 

Oxford Essential

On top, there is no going wrong with this oxford button-down shirt. When it comes to styling, there is really no unflattering way to wear this piece; tuck it in or leave it out, roll up the sleeves or leave it as is! This classic beige bag is a perfect accessory for this basic look, tying in with the two-toned ballet flats that tie the final aspects of the look together. 

Incorporate this black and gold watch into the look for an extra touch of black for an all-around elegant outfit you will keep coming back to over and over again.

8 Do’s and Don’ts of the Preppy Aesthetic

1. Classics Are Key to Preppy Style

Classics are the most essential part of the preppy style. So, your wardrobe should include:

• Polo shirts

• Khaki pants

• Shift dresses
  
  

You can mix and match them with a touch of your personality. For sophistication, you can wear a blazer or brightly colored Bermudas for a casual Monday.

2. Patterns Are Your Playground

Stripes, checks, and plaids are inevitable for preppy style. But don’t mix bald patterns with solid pieces. You shouldn’t go overboard.

3. Quality Basics Are Your New Investment

Quality is always over quantity in preppy style—the golden rule! Because of that, invest in a well-made classic trench coat or a good piece of Mary Jane. Your preppy wardrobe will be timeless.

4. Use Accessories Wisely

Less is more when it comes to preppy accessories. Use them wisely! A statement belt, a sleek watch, or a headband can completely change your look. It is all about details, but don’t overdo it.

5. Don’t Use Too Many Logos

Elegance is your key! Don’t turn yourself into a billboard. Yes, it is one of your favorite preppy dress brands, but let your style speak for itself.

6. Tailoring Matters!

A well-fitting outfit can make all the difference. It can be a classic blazer or a shift dress. Your clothing should hug you in all the right places. Wearing something too tight or oversized prevents you from having an elegant look.

7. Use Colors to Tell About Yourself

Colors are your palette now. Choose vibrant colors like mint green or a pop of coral to show your personality. A preppy look is also all about aesthetics, so bright hues are your weapon in your timeless wardrobe.

8. Too Many Trends Shouldn’t Be Mixed Up 

Remember, we said the preppy look is always about timelessness. Trends are not timeless. So, don’t mix them up!

Color Analysis

WhatColors helps you find what colors to wear based on your skin tone. Get your season based on our skin tone, thanks to 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.

How to Look like a Preppy Girl?

Achieving the preppy girl look takes a bit of time and effort, but it can be fun! Follow this step-by-step guide to get the classic prep style look that will have you:

• Feeling confident 

• Looking cute
  
  

Dressing in the Preppy Style

Preppy style is very modest and clean cut, with cute, well-fitting, and well-made items. You might have many of them in your closet already, so keep track of what you have before buying new clothes. 

Common preppy clothing items include:

• Plain colored t-shirts in white, navy blue, pastel colors, red, and neutrals

• Solid or striped blouses in bright, eye-catching colors like pink, blue and white

• Dark wash skinny jeans and khaki pants

• Plain colored cardigans in pastel or basic colors

• Navy, black, or white colored blazers

• Solid color chino shorts in khaki, navy, or white

• Riding boots, boat shoes, and basic ballet flats
  
  

Follow Preppy Brands and Bloggers on Social Media

Preppy girls tend to refer to specific brands that make clothing of their style most often. Following the brands on social media will give you ideas for how to style pieces and show you what's trendy and fashionable for this season. You don't have to buy the brand name necessarily. Some popular preppy brands to get inspiration from are:

• Vineyard Vines

• Brooks Brothers

• Ralph Lauren

• Tory Burch

• Lacoste

• Kate Spade

• Lilly Pulitzer

• Kendra Scott

• Simply Southern

• Ann Taylor Loft

• Tommy Hilfiger

• J. Crew
  
  

Budget Finds

It's easy to find affordable, preppy-style items at stores like:

• Target

• Old Navy

• T.J. Maxx
  
  

At these stores, you can get the look you want without spending quite as much money on the designer name!

Mix and Match Pieces to Create Different Outfits

One of the best parts about having a preppy wardrobe is the ability to match different pieces to create unique outfits. Layering, print-mixing, and pairing bright colors with neutrals are all techniques used to make the perfect preppy outfit. For a nice dinner out in the summer, you could wear a:

• Printed skirt

• Solid shirt to match

• A bright statement necklace

• Strappy sandals 
  
  

For school in the winter, you can wear red and white striped sweater layered over:

• A light chambray shirt

• Dark-wash skinny jeans

• Brown leather riding boots

• Ruffled socks
  
  

For school in the springtime, you can wear a pair of floral chino shorts with a matching colored polo tucked in:

• A brown belt

• A pair of boat shoes
  
  

On a casual summer day, wear a short-sleeved T-shirt, white chino shorts, and a matching pair of:

• Canvas sneakers

• Statement headband
  
  

During the colder months, wear:

• A long-sleeved shirt or blouse

• Dark wash skinny jeans

• Riding boots

• A warm headband

• Layer a fuzzy jacket over the top
  
  

Accessorize with Purses, Belts, and Jewelry

Accessories are extremely important to the preppy style, and will help pull your look together. Preppy girls tend to wear:

• Statement jewelry

• Large tote bags

• Sleek belts.
  
  

A neutral-colored tote bag pairs well with almost any outfit and is extremely functional, especially for going to work or class! Sleek belts in black, navy, red, or tan can help pull a look together and accentuate your waist. 

Accessorize Boldly

Add a statement necklace to an outfit to draw attention to your upper body and face. This is a great accessory to spice up plain outfits like jeans and a T-shirt. Wear plain earrings, like studs, to complement your look. 

For a fancier event, you can wear a matching necklace and earring set. Nautical rope bracelets and metal bangle charm bracelets are very popular for casual wear. They come in different colors and can complete a more muted outfit.

Grooming

Style Your Hair in a Sleek and Clean Look

Hairstyles for preppy girls are easy whether your hair is straight, curly or somewhere in between. Make sure your hair is clean, and use hairspray and styling mousse to tame flyaways or frizz. For a plain, cute look, wear your hair down and natural with a barrette or bobby pin holding some hair off to the side.

Accessorize a curled look with a statement headband. Plain headbands blend better with the classic preppy stereotype. Bright, colored bands might be too much. On busy days, I do sleek braids in my hair to keep it out of my face. Pull my hair into a medium-height ponytail with a bow for a quick and simple hairdo.

Wash Your Face Every Day to Prevent Breakouts

Clear skin is especially important for preppy girls because they tend to wear more natural-looking makeup. Wash your face every day with a gentle cleanser before you go to sleep. If you get breakouts often, which are sometimes inevitable, use a face wash that is specifically formulated for acne treatment. 

If you have sensitive skin, look for an unscented cleanser to avoid irritating your face, making skincare difficult.

Wear Simple Makeup in Colors that Complement Your Outfit

For preppy girls, foundation, mascara, light eyeliner, blush, and lipstick are the key components of most makeup looks. The key is to keep it simple and highlight your natural beauty. Apply your concealer and foundation in areas where you have redness or breakouts. 

You don't have to wear foundation if you're comfortable with your natural skin. Avoid using bright or dark eyeshadow colors. For a clean and classic preppy look, apply a light brown color all over your lid before applying eyeliner and mascara. Make sure your mascara doesn't clump. If it does, select a mascara with a smoother formula or use a wand with smaller bristles. 

Use a light pink or red blush on the apples of your cheeks to give you a pretty glow. Apply light pink or neutral-colored lipstick for everyday looks. On days when you want to stand out, use bright red lipstick with blue undertones.

Maintain Good Personal Hygiene

This includes showering every day and brushing your teeth twice a day. Good hygiene is a huge part of maintaining the put-together, clean-cut preppy look. If your teeth have a natural yellow tint, you might try teeth whitening. There are many different options for whitening, so you should talk to your dentist before trying a new method.

Keep Your Nails Trimmed and Wear Nail Polish if You're Comfortable with It

Avoid bright-colored nail polish because it can clash with different colors or prints in your outfit. Instead, pick light creams and pinks or a French tip style that goes with any look. If you're not good at applying polish or trimming your nails, consider getting a basic or gel manicure once or twice monthly. 

Avoid long acrylic nails, which can get dirty easily and look less professional. Gel nail polish lasts longer than a basic manicure but is slightly more expensive. You can get a manicure without polish or clear polish for regular nail maintenance like trimming, filing, and cuticle care.

Select a Light, Muted Perfume as Your Signature Scent

Choose a scent that isn't overpowering, such as a light floral or clean scent. Apply only 1-2 sprays each day to avoid smelling too strong. A good perfume is especially helpful for hot summer days when you might sweat a lot. It can help you smell good all day long!

Having a Preppy Attitude

Be Confident in Yourself

Preppy girls have brains, a sense of classic style, and an optimistic outlook. Part of the classic preppy look comes from confidence in timeless clothing. As a preppy girl, be confident by

• Holding your head high

• Speaking with conviction

• Being proud of who you are
  
  

If you have problems with low self-esteem, changing your style might be the first step to gaining some confidence.

Be Classy at All Times

Avoid using bad language, gossiping, or doing things that are considered tacky or tasteless. Be polite to others by minding your manners, and always think before speaking. It can be challenging to remain classy, especially if your friends aren't always. Try your hardest to always be pleasant and have a smile on your face.

Try Some Preppy Sports

You don't have to play a preppy sport to have a preppy style, but a few unique sports are played most often by preppy girls. Rowing, tennis, volleyball, Lacrosse, sailing, golf, track and field, ballet, swimming, field hockey, soccer, horseback riding, and cheerleading are popular sports for preppy girls.

Anything that gets you moving and makes you feel good is a positive addition to your style, so don't feel confined to a list of a few preppy sports if they don't interest you.

Be Nice to Other People

You don't have to be best friends with everyone, but you shouldn't be rude or mean to other people. Try to be:

• Pleasant

• Kind

• Cheerful
  
  

Be Kind and Helpful

Avoid:

• Gossiping

• Bullying

• Manipulating other people
  
  

If you see another person struggling, try to help them out. Going out of my way to help someone is kind and can go a long way toward making them feel good.

What Is Gen Z & Gen Alpha Preppy?

The preppy aesthetic has gone through many iterations over the years, from its wealthy, elitist beginnings to its current Gen Z version, which is:

• More colorful

• Accessible

• Inclusive
  
  

Young people have been steadily adapting the look for years, but it’s only recently that the new preppy style has gone viral on TikTok. The current preppy aesthetic is unmistakably upbeat, featuring:

• Bright colors

• Cheerful prints

• Overall playful vibe
  
  

Think: smiley faces, pastel shades, and whimsical motifs. There’s also a strong emphasis on:

• Accessories

• Like hair bows

• Colorful ribbons

• Beaded jewelry
  
  

The resurgence of the preppy style is largely thanks to Gen Z’s obsession with nostalgia and the aesthetic’s portrayal on social media.

The Preppy Look Through the Ages

For many, preppy is closely associated with clothing worn by wealthy people and preparatory school students. In the second half of the twentieth century, it became associated with attire for sports like lacrosse and rowing (for its stripes and nautical themes). It was later linked to fashion brands like Tommy Hilfiger that designed with those aesthetics. 

In the late 1990s and 2000s, there was yet another iteration of the trend: preppy became synonymous with basic styles that were more or less uninspired and in mainstream trends. In that era, brands like Abercrombie & Fitch, Hollister, North Face, and Uggs reigned. Now, the word refers to all things pink and colorful—with yet another short list of in-vogue brands in association.

3 Major Keys to the Modern Preppy Look

1. Nail the Modern Preppy Look With Pops of Pink

The vintage preppy aesthetic embraces neutral colors and a moody vibe. In contrast, the Gen Z version favors bright and cheerful colors. Expect to see lots of pink. The coquette aesthetic’s essence of empowering women and their femininity influence this color preference.

2. Mix Smart Casual Into Your Preppy Look

The old preppy outfits are formal and proper, while new iterations focus on comfort. As a compromise, aim for smart casual. This dress code can offer confidence while exhibiting a relaxed vibe.

3. Prioritize Comfort When Dressing Preppy

Yes, the typical preppy look is polished and beautiful. However, it can also feel stiff and trigger anxiety about body image. Others touch the same cloth and feel attractive. Prioritize your comfort.

15 Best Preppy Wardrobe Items to Shop in 2024

1. Pleated Midi Skirt

Say hello to the ultimate transitional piece. Every preppy wardrobe needs a pleated midi skirt. This Dunst design lands in the sweet spot between back to school and tennis round on a Sunday afternoon—which is exactly where every boat-shoe lover wants to be.

2. Stripe Rugby Knit

Preppy style and polos come hand in hand. This long-sleeved, striped rugby knit is a must-have. Tuck it into a flippy skirt and wear it with tube socks and loafers for the poshest effect.

3. Jersey Tennis Minidress

This is self-explanatory. You can look like Billie Jean King in this Tory Burch tennis dress. This is athleisure at its finest, and by that, we mean styling yourself like an athlete but being a woman of leisure.

4. Ruffled Exaggerated Collar Blouse

For the more contemporary preppy style acolyte looking for an out-of-the-box collared shirt, Ganni will undoubtedly have what you want.

5. Fleece Crewneck Pullover

Polo Ralph Lauren and labels like Tommy Hilfiger and Brooks Brothers practically invented prep and preppy style. Wear their iconic Polo player and pony—the badge of all preppy fashionistas—in this versatile pullover.

6. Kassidy Loafer

Simple, durable, and Australian-made, these Jane Debster loafers are necessary. 

7. Casual Classic New York Yankees Baseball Cap

Pop this baseball cap on with a boxy blazer, white t-shirt, and jeans, and you’ll be ready to hit the town, Princess of Wales style.

8. Julianna Cable Knit Cotton Crewneck Sweater

A cable-knit is a staple plucked straight from the official preppy handbook. Wear tucked into jeans or a checked skirt, or even better, drape over the shoulders and tie loosely at the front. It’s the ‘I’m a little too warm after my stroll around The Hamptons’ look.

9. Betty Cardigan

It wouldn’t be a preppy wardrobe without nautical stripes. This sugar-sweet cardigan from Sézane is a good place to start. It also comes in many bright colors, should they take your fancy.

10. Brown Venus Polo

This polo shirt from Scandi-label Saks Potts is as preppy as it gets. You’re missing a visor, a pair of gloves, and an equally well-dressed caddy—peak preppy fashion.

11. Silky Cotton Relaxed Shirt

Treat your collared shirts like T-shirts and own them in abundance. This Everlane design comes in a variety of:

• Neutrals 

• Preppy-friendly stripes
  
  

12. Performance Pleated Laser-Cut Stretch Tennis Skirt

This pleated mini skirt has built-in mesh shorts so you can look and live the preppy golfer’s lifestyle.

13. Nina Headband

A headband can prep-ify any outfit. This wider style from Reliquia Jewellery comes in various satin shades, but our favorite is this versatile olive.

14. 530-Unisex

These retro-style New Balance sneakers, in sandy beige, can accessorize anything from your favorite jeans to your summer midi dress.

15. x Wales Bonner Argyle Knitted Vest

A knit vest, in argyle? That’s two boxes ticked off the prep school checklist.

51 Key Influential Preppy Aesthetic Brands

1. The Oldest and Boldest: Brooks Brothers

Founded in 1818, Brooks Brothers is the oldest menswear brand in the United States. The company helped shape the preppy style, introducing classic pieces like button-down collar shirts and seersucker suits to American culture. Today, Brooks Brothers’ high-quality garments and timeless designs make it a staple for those seeking the preppy aesthetic.

2. The King of Preppy: Ralph Lauren

Ralph Lauren is arguably the most recognized name associated with preppy style. The brand has heavily contributed to popularizing the aesthetic, from its iconic polo shirts to its tweed blazers. Ralph Lauren embodies the effortless sophistication of the preppy lifestyle. The brand’s collections often draw inspiration from the following:

• Elite Ivy League lifestyle

• Nautical themes

• Traditional American sportswear
  
  

3. Tommy Hilfiger

While Tommy Hilfiger is a broader lifestyle brand, it strongly connects with the preppy style. The brand’s bright colors, bold prints, and classic silhouettes embody the preppy aesthetic. Tommy Hilfiger’s designs often feature signature elements like stripes, plaids, and nautical motifs, adding a contemporary twist to the preppy style.

4. J.Crew

J.Crew offers a more modern interpretation of the preppy style. The brand is known for its quality basics, such as chinos and Oxford shirts, but it also adds a contemporary spin with:

• Brighter colors

• Unique patterns

• On-trend pieces
  
  

J.Crew has made the preppy aesthetic accessible to a broader audience by balancing classic and contemporary elements in its collections.

5. Lacoste

French brand Lacoste, known for its iconic crocodile logo, has been a significant player in the preppy style, especially sportswear. The brand’s polo shirts are a staple in many preppy wardrobes, known for:

• Their quality

• Comfort

• Available colors
  
  

6. Vineyard Vines

Vineyard Vines is a relatively new player in the field. It was founded in 1998 on Martha’s Vineyard, a location that encapsulates the preppy lifestyle. The brand’s clothing embodies the relaxed, coastal vibe of the East Coast, featuring:

• Vibrant colors

• Nautical themes

• Whimsical prints
  
  

It’s particularly well-known for its ties adorned with unique, playful patterns.

7.  Abercrombie & Fitch

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 Classics

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 more elegant pieces
  
  

8. Tory Burch

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 Perry compartment tote bags 

• The 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.

9. Kate Spade

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

• Elegant clutches
  
  

Besides the amazing bag collection, Kate Spade offers other cute and classy accessories. These include:

• 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.

10. Lilly Pulitzer

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 a cotton-lined design. And the result?

Lilly Legacy

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. Fast-forward to more than 50 years later, and Lilly Pulitzer is still a fan 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, and fun accessories. Every piece is guaranteed to add some joy and femininity to your closet.

11. Sperry

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! 

Sperry Evolution

Eventually, in 1946, new Sperry styles were launched, and they could be used beyond the sea for everyday usage like:

• Playing tennis 

• Leisure

So 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
  
  

12. Talbots

Talbots is a preppy clothing brand that you will never stop shopping at once you start. This women’s brand was founded in 1947 by Nancy and Rudy Talbot, emphasizing modern, classy, and smile-worthy clothes for every occasion. 

Talbots are brimming with the best preppy clothes, from polished casual pieces like:

• Linen blazers

• Tweed collarless jackets

• V-neck sweaters

• Great fancy dresses
  
  

13. Southern Tide

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 and other outdoor adventures as well as for 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. Think: stripe dresses, wide-leg pants, twill shorts, and crewneck t-shirts.

14. Rowing Blazers

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
  
  

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

• Polo t-shirts

• Knits

• Leisurewear
  
  

15. Alice + Olivia

Alice + Olivia was born out of 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, and midi dresses – trust me, you will not be disappointed with the chic designs.

16. Land’s End

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 daily Sunday comfort. 

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

• Blazers

• Coats

• Fleece tops

• Chino pants
  
  

17. Sporty & Rich

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.

18. Wilfred

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.

19. Barbour

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
  
  

20 J.Mclaughlin

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
  
  

21. Sail to Sable

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, and 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.

22. Ted Baker

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
  
  

23. Banana Republic

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, and many more wardrobe classics.

24. Michael Kors

Let’s discuss Michael Kors – 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
  
  

25. 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 a good 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.

26. Coach

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

27. 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
  
  

28. Nautica

Nautica is one of the best preppy clothing brands for warm weather. It was founded in 1983 to design nautical-inspired clothes (hence the name). If you need preppy clothes for this summer, it is highly recommended that you get items from Nautica.

29. Hugo Boss

Hugo Boss is not just a preppy brand for gentlemen. This German brand also has great pieces for women. You will not be disappointed with the wide selection of modern and classy pieces!

30. Cole Haan

You might not have heard of Cole Haan, but when you go through the timeless footwear, the brand has, you will want to shop there. Cole Haan was established in 1928 to offer excellent:

• Craftsmanship

• Comfort

• Design
  
  

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.

31. 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.

32. Mango

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

• Sweaters

• Loafers

• Classic sunglasses
  
  

33. 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 the brand. It offers classic silhouettes that will perfectly align with your preppy style. 

This includes:

• Intelligent blazers

• Tailored pants

• Button-down shirts
  
  

34. 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.

35. Frank and Oak

Under-the-radar brand Frank and Oak was founded in 2012 to inspire 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
  
  

36. 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
  
  

37. Gap

You can always depend on Gap to give you the best wardrobe staples to build your preppy wardrobe. The brand was founded in 1959 to search for 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

• Seaters

• Cardigans

• Shirts
  
  

38. 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

• Many more charming clothes
  
  

39. 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 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.

40. 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 surely find a piece that speaks to your classic style, from turtlenecks to pullovers, shorts, and more.

41. Hill House

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.

42. 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
  
  

43. Drake’s

HomeDrake started life in 1977 as a haberdashery but quickly graduated to a well-respected British tailoring brand. Now, it’s an almost cult purveyor of quirky-classic preppy style that combines its excellent fabric heritage with an innate ability to style its collections for the modern man who hates the:

• Traditional suit 

• Tie
  
  

Drake’s perennials collection is a brilliantly curated trove of must-have pieces to build a preppy wardrobe around, such as the

• Five-pocket chore jacket

• Boucle wool fleece

• Lambswool turtleneck

• Shawl-collared cardigan 

• Several stunning seasonal suits
  
  

Drake also does a fine line in heavyweight Japanese selvage denim and, of course, an eclectic array of the critical preppy item, the OCBD.

44. Todd Snyder

As far as quintessentially American fashion pedigree goes, Todd Snyder has bundles of it. Before founding his eponymous label in 2011, Snyder held leading roles at Polo Ralph Lauren, The Gap, and J.Crew, so his preppy menswear credentials are bona fide. There’s a lot to like about Snyder’s aesthetic, not least his denim and chambray shirts, which add nice texture to a preppy outfit. 

Snyder also has an extensive range of chinos, jeans, sweatpants, and a great cashmere collection, all essential preppy fodder for crafting casual weekend looks.

45. Noah NY

In Noah, NY, founders Brendon Babenzien and Estelle Bailey-Babenzien have combined their love of skate, surf and music cultures with a unique take on contemporary menswear, resulting in a modern urban redux of preppy style. Noah’s forte is in producing iconic preppy pieces such as rugby pullovers, hoodies, and cardigans, alongside workwear staples such as:

• Jeans 

• Pleated pants
  
  

Using a bold color palette and abundant strong patterns, stripes, and checks, the collections are easy and fun to style with more tailored pieces such as sports coats and blazers.

46.  Hackett

Founded by Jeremy Hackett in London in 1983, Hackett was one of the original modern British tailoring pioneers, synthesizing the bespoke suits of Savile Row into a more wearable (and affordable) part of menswear. From there, Hackett evolved, incorporating a very English concept of preppiness with elevated classics cut from the finest fabrics. 

Alongside the exemplary tailoring, Hackett also created a superb range of contemporary smart casual pieces, including:

• Polo shirts

• Sweatshirts

• Gilets, in response to how the modern man’s work uniform was changing. 
  
  

Today, it’s still the go-to label for understated classics it ever was.

47. GANT

Given that it was founded in New Haven on the US East Coast in 1949, you won’t be surprised to learn that American giant GANT brings a decidedly nautical flavor to its unique preppy clothing brand. Starting out making OCBDs and flannel shirts, GANT soon gained favor with a burgeoning middle-class audience in America who were clamoring for the Ivy League style. 

A 1954 issue of LIFE magazine declared New Haven the home of the Ivy League look (it helped that Yale was on their doorstep). Today, GANT continues to evolve the preppy aesthetic with a modern maritime look rich in:

• Color

• Pattern

• Technical innovation
  
  

48. Alex Mill

Cofounded by Alexander Drexler and Somsack Sikhounmuong, Alex Mill is a brand with pedigree. Alexander is the son of Millard ‘Mickey’ Drexler – the former CEO of Gap and J.Crew and the founder of Old Navy and Madewell – while Somsack was previously design director at J.Crew and Madewell. It’s safe to assume they know something about creating classic preppy clothing. 

Alex Mill Basics

Taking a slower, more sustainable approach than the aforementioned companies, Alex Mill was founded on the principle that men don’t need new clothes but rather the right clothes. The duo initially set out to create the perfect shirt, which many would say succeeded, and have since expanded the range to incorporate all the key elements of a capsule wardrobe. 

Expect all the usual preppy fare—including OCBDs, chinos, unstructured sports jackets, polo shirts, and sweaters—all crafted using the highest-quality fabrics and designed to be completely timeless.

49. Golf le Fleur

Hip-hop has a long tradition of subverting the preppy look and nudging it into interesting new territory. This is Tyler The Creator’s take. The musician’s style has long mixed skatewear and preppy fashion, and Golf Le Fleur is his luxury tribute to the latter. 

Think on-point tennis shirts, wool varsity jackets, and pleated pants, rendered in a Wes Anderson-friendly palette of pastels and earthy tones.

50.  Beams Plus

Ametora is a Japanese word derived from ‘American’ and ‘tradition. ' It’s used to describe the wave of Japanese fashion labels that took inspiration from mid-century preppy fashion and bettered it. Beams Plus is one of the best-known, and for good reason. 

Paying homage to vintage Americana but bringing a Japanese edge to its collections, Beams is casual and rugged but elevated simultaneously. Striped tops, wide-leg slacks, and knitted polos are the brand’s staple styles.

51. Crew Clothing Company

Crew Clothing is a British take on classic American preppy labels inspired by coastal lifestyles, mixing practical pieces with smart casual staples. One side of the brand is dedicated to weatherproof outerwear and insulating layers, and the other is about herringbone blazers, Oxford shirts, and cable-knit sweaters. One of the most affordable preppy labels you’ll find, it’s also a good place to stock up on:

• Polos

• Rugby shirts 

• Chinos
  
  

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 preppy aesthetic is all about classic colors and patterns. Think navy, burgundy, hunter green, and other earthy tones. When the leaves start to change, it’s time to swap out those bright summer colors for a more muted, autumnal palette. If you want to know exactly what colors will look best on you this fall, check out WhatColors. 

This app analyzes your unique coloring to find your ideal seasonal palette and nail colors. 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.