Complete Guide to Preppy Dresses, Top Brands, & Must-Have Accessories

WhatColors

Dante Kim

September 8th, 2024

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in 60 seconds with WhatColors!

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60 seconds with WhatColors!

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When you're pulled into the allure of the preppy aesthetic, classic dresses, take little time to catch your attention. With their polished style and effortless charm, Preppy Dresses embody the timeless elements of the preppy look and serve as an essential building block for any preppy wardrobe. This article will cover how to curate a collection of iconic dresses perfect for any occasion and tell you everything you need to know to mix and match styles, top brands, and perfect accessories for a chic, classic look.

One of the best tools for achieving your preppy wardrobe goals is WhatColors' AI personal color analysis app. This valuable resource takes the guesswork out of creating personalized color palettes so you can effortlessly style your preppy dresses and other wardrobe pieces to complement your unique coloration.

What Is a Preppy Dress?
13 Preppy Dresses for the Modern Woman
10 Preppy Dresses For Work & How to Wear Them
10 Preppy Dress Brands for the Perfect Fits
6 Preppy Accessories to Complete Your Preppy Dress
Try AI Personal Color Analysis For Free Today

What Is a Preppy Dress?

Preppy dresses are a vital component of the preppy fashion style, rooted in the aesthetics of Ivy League schools and upper-class American culture. This style emphasizes classic, timeless pieces that often reflect a polished and sophisticated look.

What is preppy style, and what's the deal with preppy fashion?

Well, preppy style is more than just that—a style. Quite the contrary, it is a nod to tradition, a celebration of the classics. Defined by clean lines, tailored fits, and a color palette that could make a rainbow blush with envy, preppy style is a lifestyle—a commitment to embracing both the polished and the playful.

This style has its roots in the hallowed halls of Ivy League academia, where students rocked meticulously put-together outfits that seamlessly blended sophistication with a touch of rebellion. The campus became a runway, and the preppy look quickly transcended college gates, symbolizing timeless elegance.

Now, let's talk about elements. Classic silhouettes? Check. Colors that evoke images of autumn leaves and ocean vistas? Double-check. Patterns that range from timeless plaids to crisp stripes? Triple-check. A preppy look is a harmonious blend of these elements, creating a visual symphony that's as pleasing to the eye as comfortable to wear.

But it's not just about the clothes; it's a lifestyle. Preppy style and fashion are a mindset—a commitment to approaching life with grace and a twinkle in your eye. It's about taking that extra moment to ensure your bowtie is perfectly tied or choosing the boat shoes that can weather any storm, both metaphorical and literal.

Here's the beauty of it all

The preppy style is a chameleon. It's not confined to a gender or a generation. Men and women alike can embrace crisp button-downs, tailored blazers, and pearls with equal enthusiasm. It's a style that transcends boundaries, inviting everyone to join the ranks of the effortlessly chic.

So, whether you're a guy looking to add a touch of refinement to your wardrobe or a gal eager to channel your inner Grace Kelly, preppy styles are your ticket to a world where style meets substance, where tradition dances with the contemporary.

13 Preppy Dresses for the Modern Woman

1. The Casual A-Line Dress: Preppy Perfection

The A-line dress is a classic. You can find them in various fabrics and designs, which can also be worn for almost every occasion. Featuring a pretty periwinkle blue dress, this look can easily be worn to class or around campus on a warm day. A-line dresses are simple, easy to wear, and a preppy must.

2. The Shirt Dress: Timeless Yet Trendy

Shirt dresses are the perfect casual go-to for preppy girls. They scream “summer!”, especially with espadrilles and a lightweight cardigan. This type of dress flatters all figures, and we adore its timeless, menswear-inspired vibe.

3. The Wrap Dress: Figure-Flattering and Versatile

The wrap dress is a classic wardrobe staple chic, elegant, and figure-flattering. It’s also incredibly popular with style icons, including Kate Middleton, who famously wore a wrap dress when she announced her engagement to Prince William in 2010. This beautiful style of dress is versatile and can be easily dressed up or down depending on the occasion.

4. The Seersucker Dress: A Preppy Must-Have

Seersucker is the definition of preppy. You can see this print and its “cousin” gingham in spring and summer, just about everywhere! Preppy girls have seersucker everything. Whether it’s a pair of shorts, a blazer, or a top, we love anything made with this gorgeous fabric.

5. The Polo Dress: A Classic Look

Polo dresses and preppy styles go hand-in-hand. Popularized by brands such as Ralph Lauren and Lacoste, polo dresses have timeless designs and are very comfortable. Of course, they have a sporty vibe, so play it up with sneakers and oversized sunglasses for a comfy-chic look.

6. The Ruffle Dress: Pretty and Feminine

The ruffle dress is preppy perfection. I am a big fan of this dress because I adore the flutter sleeve and neckline. This dress style flows beautifully when you walk and is a very ladylike choice. You can’t go wrong with a piece like this!

7. The Drop Waist: Flattering and Unique

The drop-waist dress is another flattering silhouette that every preppy girl should rock. For this outfit, I combined preppy with boho chic style. This look is fantastic for fall since it uses darker colors. Also, the headband is a preppy must, so adding it to your outfit is a major plus!

8. The Lilly Pulitzer Dress: A Preppy Classic

Lilly Pulitzer is the definition of preppy, and having at least one of the brand’s dresses is a right of passage for every preppy girl. They’re beautifully made, have fun prints, and are stunning. You can’t go wrong with any dress from Lilly! Fun Fact: Jackie Kennedy and Lilly Pulitzer were close friends, and Jackie had always loved wearing iconic dresses.

9. The Fit & Flare Dress: Flattering for Everyone

Fit-and-flare dresses are so incredibly flattering. And owning one made of lace, like my pick above, makes it even more elegant. Depending on the accessories, you can quickly wear it to class or a night out.

10. The Asymmetric Dress: Fun and Unique

The asymmetric dress brings a fun twist to the preppy style. Usually, people associate preppy fashion with clean looks and classic designs. While this is true, preppy girls can shake it up with different cuts and styles. This dress features longer sleeves and sheer details and is both demure and very stylish.

11. The Midi Dress: Elegant and Sophisticated

The midi dress is an elegant and classic preppy choice. We adore the longer length, which will stand out in a sea of shorter dresses. Like my fit-and-flare pick, I selected a lace dress because it adds a sophisticated touch to any garment.

12. The Little Black Dress: A Preppy Take on a Classic

The little black dress is a classic that originated from Coco Chanel. It is a piece women of all ages and style preferences wear, love, and make their own. For a preppy take on the LBD, keep it classy with an elegant neckline and clean lines. This flutter sleeve is a fabulous twist on the traditional.

13. The Evening Gown: Glamorous Formal Wear

Preppy girls simply adore bows. I have them on sweaters, dresses, headbands, handbags, and almost everything else. They’re ladylike and so sweet. That’s why I chose this statement-making strapless gown. It’s stunning and was made for an all-out formal event.

10 Preppy Dresses For Work & How to Wear Them

1. Tweed Bow Dress Workwear Look

This Tuckernuck tweed bow dress is perfect for a chic, preppy workwear look. It has the essence of a blazer or suit jacket (even down to the bowtie!), but it’s looser structured and more feminine. It comes in three colors and patterns: light blue, jacquard, and tan. So, Tuckernuck has something for everyone, whether you’re a color queen, print princess, or neutral noble.

Wear gold bow heels and a few pieces of simple gold jewelry to style it. Sunglasses add good contrast to prevent it from looking too buttoned-up. Finally, add your favorite Gucci handbag and maybe a few pearl accessories—you’re ready for the day!

2. All Black Work Outfit

All-black outfits are flattering and can be effortlessly styled on every body type. If you struggle with what things “go together,” all-black looks are the best.

For this all-black office look, start with the double-breasted trench coat dress. Everything from the tailoring to the belt to the color to the length creates a sophisticated, corporate look that’s still sexy and chic. Pair it with your favorite black heels and sunglasses, and polish it with gold and crystal stud earrings. Simple and stylish!

3. Tunic Dress and Blazer for the Office

This look can go from work to weekend in an instant! Start with this colorblock tunic dress and nude heels. As is, the look is preppy, but it isn’t professional enough for the workplace. Add a blazer, pearl earrings, and a Citizen watch to get it there. For shoes, you could wear heels or even white sneakers.

When you leave work on Friday, remove the jacket and grab your favorite Raffia handbag for a weekend look fit for any occasion, whether it be a date night or wine in the park with your girlfriends. This is the best of the best for transitional style!

4. Print a Dress with a Pop of Color for Work

You can wear prints to the office. This black, white, and magenta dahlia dress is gorgeous and functions as a workwear dress. The print has fun colors and timeless femininity but also refined. For the rest of the look, carry your Carlton Bow Bag (great size for work), add a gold bracelet, and rock some pink shoes to bring out those dahlias. If you like a pop of color, this workwear outfit is definitely for you!

5. Gucci Wool Dress Fall Workwear Look

Preppy looks often involve high-end, quality pieces. This outfit is no different! This Gucci wool dress has a lot of texture, structure, color, and bold visual interest. That means this luxury piece does almost all the work for the outfit! All you need to do is echo those gold tones with a few understated jewelry pieces. Then, opt for black, white, or gold heels for shoes.

6. Striped Shirtdress Summer Workwear Outfit

Stripes are in every preppy girl’s closet. And a striped shirt dress? Preppy girl essential! A striped shirtdress can work for several summer occasions, including work. The dress in this look has a belt to cinch in the waist to give the outfit a more sophisticated shape. For accessories, neutral colors are best to elevate the outfit.

Depending on your workplace dress code, you could ditch the heels for my go-to espadrilles brand or white sneakers!

7. Belted Sweater Dress Fall Office Look

You can’t go wrong with this emerald sweater dress from Nordstrom for a fall preppy workwear look. (If you didn’t know, Nordstrom has some of the best workwear! Check out this post on Nordstrom work outfits for more.) The dress is perfect for that transition between summer and fall, where the mornings are crisp and the afternoons are still warm. Add neutral and gold accessories of your choice to assemble a whole look!

Additionally, I recommend you wear a belt with this one because it draws attention to the beautiful ribbing on the dress. Oh, and bonus tip: For cool fall mornings, add a trench coat! It’ll fit with the neutral accents and add to the overall look instead of distracting from it.

8. Asymmetrical Midi Dress Workwear Look

Playing with traditional corporate shapes is fun to jazz up a workwear look. For this one, grab the tailored crepe asymmetric pleated dress in camel and pair it with heeled boots or nude/black heels. The dress is preppy with the classic pleated skirt and blazer combo. But, in true Style Charade fashion, the dress turns the traditional look on its head to create something fresh!

Keep all your accessories minimal. Though it comes in multiple colors, I’d stick with neutrals for work. The shape is wild enough, and the color alone would be a little distracting.

9. Tweed Jacquard Blazer and Dress Set for the Office

This look feels like it stepped straight out of Gossip Girl, and I love that! The black-and-white jacquard dress and blazer are polished, feminine, and chic. It’s comfortable and easy to style, too! Nude or black shoes, simple gold jewelry, and a black handbag will draw it together for a perfect preppy workwear dress look.

10. Black Dress Simple Workwear Outfit

If you want something preppy but straightforward, a black long-sleeved, square-neck dress like this one is right for you. It’s preppy, effortlessly stunning, and versatile even beyond workwear looks. Go all black as we did with the trench dress, or sprinkle in some nude/natural tones. Either way, it’ll make you feel beautiful and confident!

What is WhatColors and How Can It Help You?

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

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10 Preppy Dress Brands for the Perfect Fits

1. Sail to Sable: Classic Style and Female Empowerment

Sail to Sable specializes in bright and colorful pieces perfect for summer. The company's founder, Jen, lives near me and has become a friend. She’s about to have her first baby, and you know how I feel about supporting female entrepreneurs… especially moms!

2. Persifor: Colorful, Flattering, and Travel-Friendly Dresses

Speaking of female entrepreneurs, one of my good friends, Alex, started Persifor, which makes the most flattering dresses on the planet. I’m not kidding; every single one I’ve ever worn looks great… And I’ve tried all of her cuts at this point (it pays to have designer friends, haha). The other great thing about her colorful and whimsically patterned dresses is that they never wrinkle. You can throw one in your suitcase or overnight bag and wear it the next day without steaming it.

3. Tuckernuck: A Preppy Paradise for All Budgets

This preppy online retailer carried the brands I mentioned above and so many more. The prices range from under $100 to over $700, so there’s something at every price point.

4. Gal Meets Glam Collection: The New Kid on the Block

Unless you live under a rock, you probably saw that Julia of Gal Meets Glam launched the most beautiful dress line I’ve ever seen last weekend. Her attention to detail, the beautiful colors and patterns, and pretty silhouettes have made her brand-new collection an instant hit.

5. 1901: Affordable Preppy Styles with Great Quality

I mentioned this new preppy brand in a post a few weeks ago and ordered a few more of their dresses for summer. The quality is excellent, especially for the price!

6. Draper James: Southern Prep with a Twist

Reese Witherspoon knows how to do Southern prep the right way. I love her dresses and styled one recently here.

7. Vineyard Vines: A Classic Preppy Brand

Who knew growing up in Martha’s Vineyard every year would resonate so much with these brothers that they would walk out of their desk job one day, and a couple of drinks later, they would get a big idea?! Today, the brand is the official style partner of the Kentucky Derby Polo team. Vineyard Vines makes fashionable and preppy clothing for men, women, and kids, in addition to accessories. If you love the sea, sand, sailing, or water, this style will define you – you should own at least a piece from VVs, a preppy dress perhaps, and you will probably never look back.

8. Ralph Lauren: The Original Preppy Brand

Ralph Lauren was the original preppy brand that got lost during the ride, but the company’s new CEO is hell-bent on regaling that. It also got confusing for its customers because of all the sub-brands – however, Polo by Ralph Lauren has a vast customer base, and the actual preppy fans know that this collection is going to add value to their wardrobe – which is why you will invariably find them sporting RL like a boss.

Ralph Lauren’s Polo collection was sued by Brooks Brothers, where the former once worked as a salesman. So, if you are headed in the preppy direction, get hold of Ralph Lauren, and you will be one happy soul.

9. Lacoste: The Classic Preppy Brand

If you are into preppy style or want to get started with this, you need to start with a classic Lacoste Polo T-shirt, which means you’ve done it right. Lacoste began its preppy journey 1929 on the tennis court when all this was not even a thing. But a crocodile logo on a polo T-shirt took the lead, and even before we knew it, it started resonating with preppy like nothing else ever did. Lacoste redefined, or instead defined, the idea of women wearing polo-neck T-shirts and dresses and introduced how preppy style should be done. We are forever grateful!

10. Marley Lilly: Affordable Monogrammed Preppy Items

Marley Lilly is a one-of-its-kind online preppy and monoone-of-a-kind. For anyone who is into customized gifts, but unlike the other big names, its price point sets ML apart. Preppy style has just gotten so much more affordable and fun.

6 Preppy Accessories to Complete Your Preppy Dress

1. Hair Bows: Cute and Chic

Anyone fascinated with the preppy aesthetic understands the importance of a polished look. Hair bows epitomize this notion. Bows are an easy way to create a preppy style without any effort. Simply clip a bow into your hair or tie one around a ponytail to add some preppy charm to your outfit. You can find bows in various colors and prints, making them easy to personalize to match your look.

2. Headbands: The Queen B Accessory

What would Queen B be without her headband to help her terrorize the students at Constance Billard? While that's probably not the reason you'd want one, headbands are still a chic accessory that can be handy on a bad hair day. With headbands being as popular as they are, there are various headbands you can incorporate into your look. There's plenty to choose from, from simple headbands to over-the-top embellished pieces. If you want the classic preppy look, reach for headbands with a loose bow for the ultimate Blair Waldorf look.

3. Hair Scrunchies: The Accessory for Preppy Hairstyles

If there's one constant with the preppy style, the hair is a significant component of the look. If headbands or bows aren't your thing, hair scrunchies are another accessory option to reach for. These simple pieces come in various colors and prints, making them easy to personalize. Use scrunchies to accessorize your hairstyles, or pull your hair up to get it out of your way. Scrunchies are also a great way to create sleek hair buns, a classic preppy hairstyle.

4. Neck Scarves: The Quintessential Prep Accessory

There's no more apparent preppy staple than a good neck scarf. These small pieces of fabric are a simple way of adding more color or print to your look while still keeping the outfit polished and elegant. Like other pieces, these scarves come in various fabrics or colors, making them easy to collect and style with whatever you wear that day. Opt for softer fabrics like silk for the ultimate preppy vibes. Despite the classic tied-around look, you can wear your neck scarf in a loose tie for a more casual and laid-back aesthetic.

5. Tights: The Best Cold Weather Accessory

While it's true that tights are technically a clothing piece, they're also the optimal fashion accessory for cold weather. When styled like a true preppy girl, black tights are the best accessory to elevate your look and keep you warm. Slip them underneath any pair of shorts, skirts, or dresses for a polished and sophisticated look. Bring in statement pieces like yellow or red for an extra splash of color. Finish off your tights with ballet flats and have a quintessential prep school outfit.

6. Pins and Brooches: Pretty Personalization

Brooches may have once been viewed as antiques, but recently, they've been undergoing a fashionable renaissance. With more jewelry trends gravitating towards over-the-top statement pieces, it's hard to imagine brooches and pins not entering the conversation. Although these accessories haven't been in the spotlight, they are a chic way to personalize any look. You can find vintage or unique brooches in any thrift store for something with history and meaning. Simply clip these pieces onto your jacket or dress for some extra glam.

Try AI Personal Color Analysis For Free Today

WhatColors is a super cool app that 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 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.

Get your color analysis done
in 60 seconds with WhatColors!

What Is a Preppy Dress?
13 Preppy Dresses for the Modern Woman
10 Preppy Dresses For Work & How to Wear Them
10 Preppy Dress Brands for the Perfect Fits
6 Preppy Accessories to Complete Your Preppy Dress
Try AI Personal Color Analysis For Free Today

What Is a Preppy Dress?