You’ve nailed your preppy outfit, but something still feels off. You look down at your shoes and realize they don’t match your aesthetic at all. Preppy shoes, like loafers or boat shoes, are great for achieving the classic and timeless look of the preppy style. 

This blog will help you pick the right pair for your outfit and color palette to achieve the preppy aesthetic and elevate your personal style. WhatColors’ AI personal color analysis app can help you identify your best colors to match your new preppy shoes.

​​Table of Contents

• What are Preppy Shoes?

• 10 Most Iconic Preppy Shoe Styles

• How to Style Preppy Shoes

• 31 Classic & Modern Preppy Shoes for a Timeless Wardrobe

• 12 Best Brands for Preppy Shoes

• Try AI Personal Color Analysis For Free Today

What are Preppy Shoes?

Preppy shoes feature a distinctly classic, smart style that takes inspiration from the footwear worn by the East Coast elite. Think:

• Penny loafers

• Boat shoes

• Brogues
  
  

These shoes are often constructed from high-quality leather or suede and come in various:

• Versatile neutral tones

• Color combinations
  
  

They’re the kinds of shoes you can picture on the deck of a yacht or at an exclusive country club. Of course, you don’t need to belong to an elite social class to enjoy them.

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10 Most Iconic Preppy Shoe Styles

1. The Ivy League Classic: Penny Loafers

Penny loafers are preppy shoe royalty. Made famous on - you guessed it - Ivy League college campuses, penny loafers were once a casual act of rebellion against stricter societal dress codes.

How to Wear Men's Loafers?

A social chameleon, the loafer is the most straightforward, smart-casual player in this lineup. A pair of black leather loafers or deep burgundy will rarely steer you wrong regarding preppy style. Choose a chunky silhouette, such as our Chorleywood loafers, for a modern update.

To wear confidently, opt for socks and loafers to maintain the quirky side of preppy style. Pair with straight-leg chinos and a varsity jacket for a touch of nostalgia.

2. Chunky Lace-Ups Are a Must-Have

Be it a brogue or our Cheadle lace-up shoes, a chunky lace-up is a non-negotiable for building your preppy style. Crafted in suede, Cheadle is structured with a piped toe seam and dual eyelet lacing.

A chunky sole will add definition and weight to your look. Don’t be afraid to experiment with matching and contrasting clothing textures.

Vintage Fabrics

Tweed, flannel, houndstooth, and herringbone are typically used in hunting-sports clothing, reflecting the preppy style's vintage and sports-based origins.

For heritage-inspired prep, choose a loose-fitting sports jacket in the above fabrics. To complete the look, consider a patterned sock.

3. A Sports Kit is Essential

A preppy wardrobe wouldn’t be complete without adding a cup sole trainer. Take the Sutton leather trainers, for example. Traditionally constructed in leather with a flexible rubber sole, Sutton takes inspiration from the styles of days gone by, updated in a modern iteration set to withstand the test of time.

The safest option for those looking to dip their toe into preppy style without fully committing to the aesthetic, it’s long been understood that a classic white trainer is a smart-casual staple. If you want to keep it at least a little preppy, an OBDS (an Oxford button-down shirt) and chinos make smart-casual dressing as easy as strolling across the college green.

4. Modern Mary Janes for Women

When we say preppy, you’d be forgiven for thinking back to your:

1. Old school uniform shirt

2. Skirt

3. Mary Jane shoes.
   
   

However, Mary Janes has experienced a renaissance. They are now presented in chic silhouettes suited to the modern woman and the pace of contemporary life.

Modern Mary Janes

From the playground to the halls of haute couture, modern Mary Janes, including our own Luciana, subvert the traditional child-like style: note the addition of sophisticated details, such as a square toe and slight block heel.

Style with an oversized blazer and a mini skirt to maintain Luciana’s modern appeal (bonus points for white socks).

5. The Classic Loafer

There are two routes to achieving a preppy style for women's loafers: 

• The heeled loafer

• The chunky-heeled loafer
  
  

Genevra are our chunky, heeled loafers carved from smooth leather. They have a piped toe and chunky chain detail. Let midi skirts in plaid or dogtooth patterns be your sartorial guide when styling chunky heeled loafers.

Chunky Loafers

The second route sees classic leather loafers elevated on a rebellious chunky sole. Darra features:

• A cleated sole

• Grained leather upper
  
  

Contrast with softer fabrics, such as a cable knit jumper and an oversized sports blazer with striped detailing.

6. The Jack Rogers 

Inspired and commissioned by my favorite style icon, Jackie Kennedy, Jack Rogers sandals are the definition of preppy. Their intricate stitching is beautifully done and very elegant.

These sandals are everywhere in the summer! They come in so many different combinations of colors and are flawless. And when fall and winter roll around, this fantastic brand also makes sneakers, flats, and boots, so be sure to check those out!

7. The Riding Boot

An equestrian theme inspires many preppy styles; these boots are no exception. They are sleek and simple yet incredibly beautiful. While you can wear riding boots many times throughout the year, I enjoy wearing them the most in the fall. Wear jeans and a classic sweater, and you are ready for class!

8. The Classic Pump

The classic pump is a shoe that you will love and enjoy throughout every stage of your life. It’s perfect for internships, jobs, or going out with friends. Ladies, shoes like these never go out of style; in many cases, that is a trademark for preppy pieces.

These pumps were popular throughout the 20th century and remain fashionable today. Shoes like this are worth the investment.

9. The Hunter Boot

These wellies are the perfect rain boots! Preppy girls love Hunters because of their incredible quality and timeless design. 

Hunter rain boots are the go-to shoe for rainy days. They keep your feet dry and are super stylish. These fantastic shoes come in various colors so that you can be playful with them.

10. The Open-Toed Heel 

These are classic preppy heels. They are simple yet sophisticated and bring an elevation boost to any outfit! While this style comes in various colors, I enjoy the nude version because it’s elegant. 

You can pair them with just about anything and for every occasion, from a simple pair of jeans for an afternoon at a café to an elegant dress for an evening out.

How to Style Preppy Shoes

Preppy shoes are simple but elegant enough to complete your look and make you feel awesome. Some of the best shoes for preppy outfits for women include the Mary Jane heels. They are versatile and comfortable and go with almost anything from:

• Jeans

• Sheath dresses

• Slacks

• Blazer outfits
  
  

Ballet Flats

Ballet flats are the next best thing, as they go with almost any preppy outfit without any effort at all. The upside of ballet shoes is that they come in a wide array of colors and patterns. Loafers and oxfords are perfect to pull off the British boarding school vibe. These may not be suitable for winter, but they are well-suited for fall and pair very well with:

• Jeans

• Slacks

• Skirts
  
  

Choose from a classic light brown to go with everything in your closet or a bright red or leopard print to excite you. This list is complete with boat shoes! Boat shoes are great for women's casual preppy outfits. They are the perfect companion for boating, walking around town, and everything in between. They are a classic style shoe that has lasted the test of time.

Sizing up Style Patterns for Preppy Outfits

You may not know this, but patterns play a huge role in preppy outfits. For women, nudes, whites, pinks, and navy are the most common colors. Patterns include florals, plaid, polka dots, and stripes, all common on skirts, pants, tops, and accessories. It’s also easy to pull off a bold look with patterned dresses. 

For a perfectly preppy outfit balance, match patterns clothing with plain colors. The navy & white stripe combo is perhaps the most famous pattern in the prep world. Some even consider it a solid, as it is so prevalent and worn all year round. Stripes have evolved from boat neck tees, chunky knit sweaters, and pleated silk dresses.

Color Me Preppy

We may have mentioned some basic colors above, but for a preppy outfit, it’s almost limitless. You can pull off:

• Yellows

• Red

• Green

• Blue

• Pink
  
  

Take a page from Prep Queen Bee Lilly Pulitzer’s book and splash a colorful print on an ensemble. You will look and feel happy instantly. Patterns, prints, and colors are all great - but what about critter embroidery? Your beloved golden retriever, favorite martini cocktail, or holiday motif will have you making friends and inside jokes everywhere this fall and holiday season.

Accessorize Your Preppy Outfits Like a Pro

The best part of a preppy outfit for women is the right accessories. Pearls are the jewelry to go with. Hats and headbands are a common pair. Then, add light scarves, dainty wristwatches, and tights to complete a perfect look: Jackie O and Blair Waldorf.

Preppy Outfits Tips for Men

Men are included in this trend, but the main feature. All preppy styles derive from menswear:

• Corduroys

• Sweaters

• Loafers
  
  

The preppy style will definitely make you stand out. Here are a few tips for men who want to rock this look.

Preppy Style Shirts

One of the quintessential preppy style elements is the button-down shirt, especially when worn as a business casual outfit. Polo shirts are best suited for less formal outfits but are also great for formal events. Collared polo shirts are some of the signs that you are prep.

Oxford Shirts

A formal ensemble with the button-down oxford shirt will require a necktie, but ditching the tie and replacing it with a sweater can give you a more casual look. For a refreshing and novel preppy look, go with the seersucker shirt. 

It works well for a formal look, especially when tucked in. It's perfect for hotter summer days, and I suggest a full seersucker suit!?

Preppy Style Sweaters and Blazers

Sweaters are the epitome of preppy outfits for men. They can be worn over shirts, under blazers, or tied around your shoulders. Choose from a classic crew neck, v-neck, cable knit, or cardigan. All sweater options look exemplary when paired with a button-down oxford shirt and tie. 

Cotton, cashmere, and wool are the best fabrics for sweaters. Solid colors will last a lifetime, but argyle prints and stripes are fun ways to jazz up your routine. Blazers are synonymous with the preppy style, especially the timeless navy blazer, which always looks fantastic. 

Navy Blazers

A solid navy is such a common choice because it comes off as smart and nautical. Single-breasted blazers with gold buttons embody the preppy style perfectly, and pocket squares make them look even better. There is a wide variety of materials, such as wool and poplin. A tweed blazer is sharp for Fall and exudes the collegiate prep style of yore. Throw on a bow tie and oxford shoes, and you will be sure to impress.

Chinos and Go to Hell Pants

Nothing screams preppy like chinos. Chinos need to be well-fitting and go well with the Oxford shirt. You can pull them off with a sweater or blazer, making them a tremendous preppy outfit choice. Throw a cuff in the hem to show off your bare ankles and loafers look.

Critter Pants

The shirt will be a good option for keeping warm in winter, but the blazer can take fall. Go-to-hell pants are for the bold; they need the courage to pull off. But if you feel up to it this fall, why not have fun with clothing? 

They come in bright colors like green, yellow, and red with loud, audacious patterns. If you wear these, tone down the rest of the outfit to achieve some semblance of the overall look. Critter pants are the epitome of this style, and you can pick one that fits your interests or events. Holiday-themed embroideries are the hit of all parties.

Preppy Shoes for Men

Your shoes are the conversation setter for your outfit, so you need to get this right. Loafers are the first choice as they are light, super comfortable, and easy to match with anything. The Penny Loafer is an incredible choice for your Fall escapades.

Boat Shoes

Boat shoes are the next best thing, and they also go well with pretty much any preppy outfit. The Bridle Bit Driver is the most iconic shoe - suitable for all seasons and will never go out of style. 

Popularized by Gucci, the harness or horse bit ornament has become a status symbol and a coveted look. Our latest obsession is the personalized tri-colored bit Bearing on the classic Deck Driver or Moc.

For the Accessories

Preppy styles require bold and colorful accessories. The conventional collegiate rep stripe ties are great, but you can also go with:

• Plaid or madras ties

• Animal print silk ties

• Knit ties
  
  

Stick with a light or dark brown for a book or work bag. Add your heat-stamped monogram for an Uber prep touch. Socks are necessary at some point in the colder months, so opt for a classic stripe or fun motif to get you through the workday. 

WhatColors’ Color Analysis

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 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.

31 Classic & Modern Preppy Shoes for a Timeless Wardrobe

1. Snazzy Preppy Sneakers: New Balance Made in the UK 991

New Balance is a classic preppy staple that can easily crossover to all walks of life. In some ways, this is the ultimate preppy shoe brand, from its New England roots down to the Steve Jobs thing. These are constructed in the UK, adding a layer of awesomeness.

2. Sleek & Stylish: Veja Recife Chrome Free Leather White Black 

Veja has become a favorite for the guy who wants to put a new spin on the preppy look by wearing a progressive, sustainable brand. Veja shoes will give you that sleek, not-trying-too-hard look.

3. NikeCraft Tom Sachs General Purpose Shoe: Nike Tom Sach's General Purpose

It is the coolest shoe you can buy. It also works great with your preppy outfit. I promise you will see me wearing this shoe at some point. Lucky for you, while the Mars Yard was borderline unobtainable, according to Sachs and Nike, this will be restocked regularly.

4. Sophisticated & Classic: Officine Générale Brown Suede Mika Penny Loafers

The penny loafer is a preppy shoe staple for men, and it is having another big moment. Pair it with crisp selvedge denim to get an elevated preppy look. Officine Générale makes fantastic shoes, including these.

5. Minimalist Sophistication: Common Projects Track

Common Projects is one of our favorite shoemakers, and for good reason. These sporty runners feature the minimalist Common Projects aesthetic in a highly functional design.

6. Classic Boat Shoes: YUKETEN Full-Grain Leather Boat Shoes

Yuketen hand-makes many of its shoes in Maine, harkening back to the glory days of the craft in places like Skowhegen and Dexter. These full-grain leather boat shoes can be your go-to kicks for preppy situations.

7. Sustainable Style: Saye Modelo '89 Vegan

These are beautiful, sustainable shoes from Saye. Pull these out to get the maximum laid-back, preppy style. I like these shoes.

8. Versatile & Functional: Birkenstock Clogs

Birkenstock clogs are some of the most versatile shoes for any dress style. Preppy is no different—these will elevate any preppy look. These green ones will undoubtedly help you own the day with an extra splash of color in suede.

9. Preppy Summer Style: Soludos Mimosa Platform Smoking

10. Preppy Pumps: Sam Edelman Hazel Pumps

11. Classic Preppy Sandals: Jack Rogers Hollis Flat Sandal

12. Stylish Tory Burch Slides: Tory Burch Bianca 45mm Slide

13. Cute & Classic Wedges: Kate Spade New York Giovanna Espadrille Wedge

14. Timeless Mary Janes: Gucci Sylvie Pointy Toe Mary Jane

15. Sophisticated Flats: Kate Spade New York Nicole Leather Flats

16. Classic Loafers: Tory Burch Amelia Backless Loafers

17. Elegant Pumps: Dolce & Gabbana Crystal-Embellished Printed Glossed-Leather Pumps

18. Preppy Gingham: Manolo Blahnik Gingham Pointy Toe Pump

19. Floral Flats: Salvatore Ferragamo Varina Floral Flat

20. Driving Moccasins: Tod's Gommini Leather Driving Moccasins

21. Classic Pumps: J.Crew Lucie Pump

22. Slippers with Personality: Charlotte Olympia Kitty Houndstooth Slippers

23. Classic Summer Espadrilles: Castaner Jean Espadrille

24. Rockstud Sandals: Valentino Rockstud PVC Flat Thong Sandal

25. Ankle Booties with Bling: Jimmy Choo Hanover 65 Crystal-Embellished Suede Ankle Boots

26. Preppy Rain Boots: Burberry Zane Signature Check Rain Boots

27. Scalloped Flats: Chloe Lauren Scalloped Suede Ankle-Strap Flat

28. Ruffled Mules: Loeffler Randall Langley Ruffle Pointy Toe Mule

29. Elegant Bow Sandals: Stuart Weitzman Ally Bow Sandal

30. Classic Patent Leather Pumps: Salvatore Ferragamo Vara Patent Leather Pumps

31. Boat Shoes: Sperry Women's Customizable Authentic Original 2-Eye Boat Shoe

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7 Preppy (& Practical) Shoes for Toddler Boys

1. Adidas Stan Smith - The Preppy Classic

Adidas Stan Smiths are a timeless classic and my favorite preppy toddler boy shoes. These were the first shoes I got for Teddy, and I loved them. They were easy to get on and off him and matched everything in his closet (lots of grey, blue, white, and green). 

I also like that this more adult style doesn’t scream toddler. The Stan Smith style ranges from baby crib shoes to adult sizes too. The crib shoes have elastic laces that are easy to wear. The toddler version has velcro, the little boy version has elastic laces, and the big kid version has regular tie laces.

2. Adidas Superstar - Another Iconic Shoe

These are another great alternative from Adidas. They are more sporty, but many of my friends love these little boys. Just like the Stan Smiths, they have the same style for all sizes and life stages, from baby crib shoes up to adult sizes.

3. Converse - Great for Multiple Kids

A friend told me that she loves Converse for her kids because they are gender-neutral and can be passed down and worn by multiple siblings. This is a HUGE thing to consider if you plan on having multiple children. These white Converse are great for that reason. Just make sure you get a pair with elastic laces or velcro. 

I had a pair for Tedy that were lace-up, and getting on and off him was a nightmare. I ended up selling them and getting the Stan Smiths instead.

4. See Kai Run - Affordable and Quality

When I was first looking for shoes for Teddy, the number one more recommended brand I heard about was See Kai Run. They are great for chubby baby feet and are much cheaper than the other brands. 

Teddy had a pair of See Kai Run boat shoes that he has since grown out of. You can find them at Nordstrom and Nordstrom Rack with additional discounts.

5. Sperry Boat Shoes - Preppy and Nautical

Speaking of boat shoes, I recently discovered that Sperry makes toddler shoes. Yes, teeny tiny Sperry boat shoes are a thing, and they will soon come to my household! Jk, I will get Teddy a pair for next spring and summer.

6. Hunter Boots - Perfect for Rainy Days

Little boys need a decent pair of rain boots to be accessible and to splash in all the mud their little hearts desire, in my opinion. Hunter rain boots are the gold standard when it comes to rain boots. I’ll order Teddy a pair for the winter so he can still play outside, even in the rain. They make toddler-sized rain boots, both with or without pull-on straps.

7. Loafers - The Dressy Option

I wanted to include a pair of dress shoes for toddler boys quickly. I prefer loafers for Ted over oxfords or anything that laces up. These look nice for dressier events like church or weddings but could also be worn with shorts and a nicer button-up for semi-formal events. 

12 Best Brands for Preppy Shoes

1. Sperry: The Nautical Preppy Shoe

Sperry has been producing its famous boat shoes since the 1930s. The Authentic Original™ Boat Shoe is particularly iconic. These shoes are a must-have for any preppy wardrobe, especially if you like sailing or spending time on the water.

2. Brooks Brothers: The Classic Dress Shoe

Brooks Brothers is known for its high-quality dress shoes and loafers. These timeless styles align perfectly with preppy aesthetics. You can’t go wrong with Brooks Brothers when dressing for a country club or holiday gathering.

3. L.L. Bean: The Rugged Preppy Footwear

L.L. Bean is renowned for its rugged yet stylish footwear. The brand's duck boots and casual shoes are practical choices for a preppy look. They pair well with chinos and flannel for a classic autumn outfit.

4. J.Crew: The Trendy Loafers

J.Crew offers a variety of preppy styles, including loafers and oxfords, that blend modern trends with classic designs. The preppy aesthetic is all about looking polished and put together. J.Crew shoes will help you achieve that look while incorporating the latest styles.

5. Vineyard Vines: The Coastal Preppy Brand

If you love the coastal preppy lifestyle, you’ll adore Vineyard Vines. This brand embodies the aesthetic, offering a range of shoes that complement its vibrant clothing line.

6. Jack Rogers: The Go-To Summer Sandal

Known for its classic sandals, Jack Rogers is a go-to for preppy summer footwear. The brand's iconic flat sandals, featuring the signature medallion, are a staple for preppy females. They look great with everything from shorts to sundresses.

7. Tory Burch: The Chic Preppy Flats

Tory Burch offers a variety of stylish flats and loafers that are chic and suitable for a preppy outfit. The brand’s designs often feature bright colors and bold patterns for a fun twist on classic preppy styles.

8. Sam Edelman: The Stylish, Comfortable Shoes

Sam Edelman features a range of stylish and comfortable shoes, including loafers and pumps that fit well within the preppy style. The brand is known for its trendy designs that are perfect for various occasions.

9. Kate Spade New York: The Playful Preppy Footwear

Known for its playful and colorful designs, Kate Spade New York offers shoes that add a fun twist to preppy outfits. If you want to incorporate a bit of personality into your look, this is the brand to turn to.

10. Gucci: The Luxury Loafers

While on the higher end, Gucci's loafers and other styles often feature classic designs that align with preppy aesthetics. Consider this luxury brand if you want to invest in quality shoes that always stay in style.

11. Lacoste: The Sporty Preppy Shoes

Lacoste offers sporty yet stylish options that fit the preppy look, especially with its polo shirts and casual shoes. The classic tennis shoes are perfect for a relaxed but put-together appearance.

12. Crew Clothing: The British Preppy Brand

Crew Clothing is a British brand providing a range of preppy styles, mainly coastal and nautical themes. The classic shoes will help you achieve a timeless look that stays in style.

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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 helps you get the perfect colors for 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.