Fall is here, and it's time to update your clothes. Picking out new outfits isn't as easy as it used to be. Styles change, and we want to look more polished and classy now. This article will help you dress better this fall. We'll talk about the, preppy aesthetic, preppy style and how you can wear it.

What’s more, we’ll show you how to use WhatColors’ AI personal color analysis app to help you refine your preppy girl style so you can build an elegant, timeless look that flatters your unique coloring.

Table of Contents

• What Is a Preppy Girl?

• What Is a Preppy Girl’s Personality?

• How to Be a Preppy Girl in Real Life?

• 9 Classic Basics Every Preppy Girl Needs

• 25 Top Preppy Girl Outfit Ideas in 2024

• Preppy Little Girls’ Clothes That Are Practical Too

• Do Preppy Girls Wear Jeans?

• Try AI Personal Color Analysis For Free Today

What Is a Preppy Girl?

The preppy style evolved from the clothing worn by the Ivy League elite and their peers in the Northeastern college scene. Preppy comes from the word preparatory, as in preparatory schools that send kids to Ivy League colleges. The term first appeared in the 1960s, when kids who wore trendy, expensive clothes to college got a name: The Ivy League. 

The look got much attention over the next few decades, especially after being featured in the 1974 edition of the influential style guide, The Official Preppy Handbook. Author Lisa Birnbach has seen this all before. The author of The Official Preppy Handbook, which went old-world viral in 1980, is peering out from her proverbial Lacoste visor at yet another preppy revival.

Preppy Revival

Whether it's Emma Chamberlain going full dark academia at Paris Fashion Week, Zendaya mixing tennis core and 2000s prep in the upcoming Luca Guadagnino film Challengers, or boat shoes, of all things, popping up at Miu Miu, there's no doubt that the aesthetic has made its umpteenth comeback. But what does preppy style signify now, and how did an aesthetic that once felt niche and exclusionary take over the world? 

"It's much more exciting than it was in 1980," Birnbach says of today's preppy universe. "The audience keeps getting more fashionable and younger." And the style is far more legible, as well. When she first published the book, she says, I had to begin every single interview, whether it was print or TV or radio, with Lisa, what is a preppy? as though I were explicating a new species to a zoology class.

Privacy vs. Sharing

Prep 1.0 was private and quiet, and those were different times. Without digital space, there would have been no oversharing. Privacy was understood, and it was a currency."  Now, "I have kids in their 20s and 30s, and they would no sooner not share an experience. 

You do something, you share it, you put it online. So imagine not having that ability and valuing discretion, which is what the preppy community was like."

Evolution of Prep

It also took a lot of work to access. In the early '80s, if you wore these clothes, you either ordered them through the mail or physically went somewhere and brought them back, whether Bermuda or Darien, Connecticut. The fit, too, could have been more precise. The garments were baggy and rumpled, not meant to look trendy.

By the time Birnbach's 2010 follow-up True Prep rolled around, "there were so many new brands, I felt like a godmother. Everything fit well, in bright colors instead of the four: camel, red, navy, gray, and white." By then, significant designers like Tory Burch and Thom Browne were putting their spin on the aesthetic, one that had wide-ranging ripple effects. 

(Thanks to Browne's influence, Birnbach says, "I haven't seen a picture of a groom at a wedding wearing socks in five years.") 

Global Preppy Movement

The style has become a global lingua franca, "a default way of dressing for people all over the world." When Birnbach embarked on an international tour for True Prep, she found preppies of all stripes from Japan to France. 

That global aspect was particularly evident this season, as the style was filtered through Miuccia Prada's Italian tailoring lens, Dries Van Noten's eccentric Belgian eye, and Maison Kitsuné's Japanese-French sensibility. One aspect of the current prep movement, with its high-end takes on polo shirts and boat shoes, feels at odds with the original ethos. "Preppies are frugal," Birnbach points out.

Prep and Affordability

"We're getting used to a plate of spaghetti costing $35 in a restaurant. Spaghetti and tomato sauce! That's extortion. In my opinion, a $1,000 white cotton shirt is also the other side of preppy. It's just too much." 

Price tags aside, people opt for safety in times of uncertainty. Birnbach calls preppy fashion comfort food for anything that confers status, à la the quiet luxury and stealth wealth trends.

Prep as Comfort

She mentions the emotional toll of the pandemic and adds, "I think we're still at the beginning of that. We're still determining if it's over. And to be honest, things are emotionally worse right now as we're on a wobbleboard waiting to see if our democracy will survive the election. I'm speaking of Americans, but the whole world is in flux. 

And I think throwing on a cardigan or the oldest pair of corduroys you own" is the sartorial equivalent of putting down an anchor. "It's about finding something solid and familiar." For many who are now hopping onboard the trend, she believes, it's "not about fashion. It's just about wearing something that endures.

Prep as Ritual

And for others, it's this minute, right now. Then they'll wear [the clothes], take good care of them, and sell them on The RealReal in eight months. Regardless of your camp, rituals and rules (yes, even in the form of office clothing) are more sacred. Frustrated by vague directions to find your style, people are now looking to be told how to dress, crave style guidelines, and are nostalgic for the traditional uniforms of another time. 

"I heard myself say to somebody the other day, 'I want to get dressed. I want to put on a dress and heels and go to dinner.' Now, that rarely happens," Birnbach says. "No matter how much you pay for a plate of spaghetti."

The Signature Elements of Preppy Style

Gossip Girl made the preppy look cool. The show, which aired from 2007 to 2012 and followed the lives of privileged teenage Upper East Side New Yorkers as they moved from public school to university and beyond, is getting a reboot (which starts in July), and HBO has released its first look at the cast in action. 

While there's a chance you neither care about HBO's revamped show nor watched the original, there's no denying that a glimpse of that collegiate prep that becomes synonymous with Blake Lively's Serena van der Woodsen, Penn Badgley's Dan Humphrey, Chace Crawford's Nate Archibald, Ed Westwick's Chuck Bass, and Leighton Meester's Blair Waldorf warmed your cockles a little, right?

Prep Reboot

With the rebooted cast, which includes up-and-coming talents Thomas Doherty, Jordan Alexander, and Evan Mock, there will be more of the same. Those uniforms, consisting of untucked shirts, cotton-blend navy blazers, beige chinos, and striped club ties, are back (although things have been brought into 2020, and eagle-eyed sneakerheads will be pleased to see a pair of Beyoncé's Ivy Park x Adidas kicks in the show). 

In a world awash with streetwear (who isn't talking about Supreme right now?), we're more than ready for a return to 2010's heyday of prepster goodness (taken from the fashions of those old northeastern colleges) when Polo Ralph Lauren shirts, J Crew's oversized rugby tops and cashmere sweatpants tucked into white socks were the looks du jour. We aren't alone, either. 

Prep Goes Mainstream

Tyler, The Creator, Pharrell Williams, and A$AP Nast are just three of the famous figures who are behind a new movement of preppy dressing, regularly taking to the 'gram to show off their:

• Penny loafers

• Ankle-grazing chinos

• V-neck sweaters

• Knee-length schoolboy shorts 

• Sweater vests

Big brands such as Aimé Leon Dore and Lacoste are sticking to their roots, pushing for prep through polo shirts, striped scarves, supple leather loafers, fleece dove-hued joggers, and cardigans in flashes of the Ivy League signature green and white.

Prep Revival

Collegiate-centric US brand Rowing Blazers recently dropped a collection dedicated to the just-out-of-university style of the late Princess Diana, which has naturally been a social media hit and is full of shawl-collared blazers, striped Oxford shirts, and varsity hoodies that even have Are you a preppie? Printed on them. 

And with just over two months until Gossip Girl 2.0 lands on our screens, there's never been a better time to dig out that RL top and throw on some Bass Weejuns.

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What Is a Preppy Girl’s Personality?

Personality traits often associated with preppy girls include:

• Being well-mannered

• Confident

• Ambitious

Think of the typical girl-next-door types you see in movies and on TV. Preppy girls may seem like they have it all together, and that’s because they usually do. They tend to come from affluent or academically focused backgrounds, which helps them get ahead in life. 

Beyond the Stereotype

While it may be easy to label preppy girls as boring or snobby, the truth is that these stereotypes miss the mark entirely. There’s much more to preppy girls than their polished exteriors. They have unique interests that may or may not align with popular culture. Preppy girls also have a distinct sense of style that allows them to stand out from the crowd. 

Most importantly, they are kind and welcoming to others, so don’t be surprised if they invite you to join their group.

What Is Preppy Style?

The term preppy refers to the style associated with the children of the elite, particularly those attending preparatory schools. The look is characterized by classic, clean-cut pieces that can be easily mixed and matched. Think:

• Polo shirts

• Khakis

• Cardigans

• Boat shoes

Modern Preppy Style

While the look can be pretty colorful, there’s a certain understated quality, as if it’s been plucked right off a well-organized shelf. The style has returned recently, with a new generation of teens breathing fresh life into the aesthetic. 

Today, preppy style embraces the old and the new, mixing vintage finds with trendy pieces from popular brands like:

• Lilly Pulitzer

• Ralph Lauren

• J. Crew

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How to Be a Preppy Girl in Real Life?

The Preppy Essentials: What You Need to Get the Look

You must first track down the right clothes to adopt the preppy look. Preppy aesthetics revolve around classic, timeless pieces with a sophisticated flair. The look is polished and avoids showing too much skin or looking overly sexy. Here are the essential items to shop for to get the preppy look:

Polo Shirts

These collared staples, which come in short and long sleeves, look great on their own or layered under a sweater or cardigan.

Sweaters

Cable-knit styles, cardigans, and pullovers are all great options. Look for classic colors or preppy patterns like argyle.

Blouses

Choose simple styles that are well-tailored. Avoid anything too trendy.

Khakis

These can be in shorts, capris, or full-length styles.

Quality Denim

Dark-wash jeans can be part of a preppy look, especially when paired with a blazer or sweater.

Dresses

Tea or A-line styles are best. Look for classic patterns like plaid or subtle florals.

Accessories

Think classic, understated, and even a little vintage. A string of pearls or a simple pair of stud earrings will do.

Shoes

Go for quality over quantity. Opt for a few classic pairs, such as loafers, ballet flats, and sneakers.

Where to Shop Preppy

You can shop for preppy clothes almost anywhere. Popular retailers include:

• J. Crew

• Ralph Lauren

• Vineyard Vines

• Tommy Hilfiger

You can find adorable preppy clothes at many stores. Depending on the look you are going for, you can get name-brand clothes like:

• Hollister

• Abercrombie

• Aeropostale or find equally cute outfits at thrift stores

Thrift Store Finds

If you tell them, you will only know how many previous owners your clothes have had. If you are low on cash, check out discount stores such as:

• Goodwill 

• Plato's Closet

They will almost always have designer clothes for a fraction of the cost!

Classy Girls Get Good Grades

Being preppy is about more than just looking the part. It's also about acting a certain way. Preppy girls are often high achievers. To get the look:

• Try to emulate their academic performance. 

• Opt to learn and do well in school. 

• Always strive to get good grades in school. 

• Listen to the teacher, take short but effective notes, ask questions, and always do your homework. 

If you can't attend a private school, take advanced placement (AP) or accelerated courses in almost everything possible. If your school offers electives, choose preparatory vocational training classes (such as culinary, architecture, or agricultural science) rather than an easy A class. Taking a student council or a physical education class is also good. Try to focus your high school career on getting good grades and participating in:

• Clubs

• Sports

• Organizations

Prioritize Your Studies

It's okay to have fun sometimes, but it's essential to realize that school is important. Use your school's resources (pre-ACT/SAT classes, tutoring, library, etc.) and try your best to earn scholarships! Take a foreign language if your school offers it. Many universities require 2-3 years of a foreign language for admission, and you will look very educated. 

Preps take education very seriously and can always converse about any topic; they are well-rounded. Reading is very classy and helps you expand your vocabulary and learn more. Make it a goal to read at least 2 books a month.

Classy Girls Have Good Manners

This is the most important aspect of being preppy. Real preps are always polite and kind. Preps are never rude, mean, or unpleasant. They are never bullies and should always be able to make others feel good about themselves. Don't get too obnoxious around strangers. Just say a simple and polite Hi.

Mind Your Manners

When eating dinner with others, keep clean and keep a manageable mess after you're finished. Preps do little to no cursing. They treat adults with respect and follow their rules. They surround themselves with:

• Positive

• Kind people

• Much like themselves

You can go to people with a problem, and they will help. Try not to swear or do anything unhygienic in public. Always say please and thank you, and greet your elders. Stay somewhat reserved and considerate.

Classy Girls Expand Their Vocabulary

Slang words and curse words are not polite or classy. You don't have to use highly complicated words for every sentence, but it's good to know some classic language that most don't use nowadays. You can do this by reading and listening to people with a wide vocabulary talk.

Classy Girls Are Good Conversationalists

Don't talk about partying, drugs, smoking, or anything rebellious. Talk about casual stuff like homework, what you're doing next week, what books you've been reading/what music you've been listening to, etc. Try to be a good conversationalist. Be a good listener and make eye contact. Try to listen more than you talk.

Classy Girls Are Kind and Courteous

Classy people are intelligent and elegant but aren't unapproachable or arrogant. Learn when to stand up for yourself or others and be assertive, but never be bossy or rude. Avoid people who say bad things about you, and avoid disloyal friends. Always offer honest compliments and smile, and offer to do favors with nothing in return.

Find Good Role Models

Women such as Meryl Streep, Princess Diana of Wales, Audrey Hepburn, and Jackie Kennedy—women with class and grace—are the kind you should look up to! 

9 Classic Basics Every Preppy Girl Needs

Do you ever need certain staple pieces in your closet that will take your style to the next level? Trust me, every fashionista has felt that way at some point. That’s why I have compiled a list of preppy basics to add to your wardrobe, including my go-to preppy outfit!

1. A White Oxford (Button Down)

Every preppy/classy girl must have a white button-down in their wardrobe. This piece can be used for years and spans all seasons. Adding a collared shirt under a sweater will polish your look much more. There is something so sophisticated about a crisp button-down- which is why every prepster needs this staple piece.

2. Black Pants

Black pants are so classic-look to celebrities like:

• Audrey Hepburn

• Grace Kelly

Not only do these slim your figure, but they go with everything. I prefer the Pixie Pants from J.Crew, but a pair from Old Navy or elsewhere will do just as great!

3. A Neutral Bag/Tote

Yes, we all love those super cute and colorful Kate Spade purses (I have one in bright hot pink!). You need a purse that can go with just about every outfit. I like this tote from Barrington Bags. It’s great for:

• Carrying laptops

• Books

The tote bag is a suitable alternative to the backpack for college students seeking a more polished appearance in the classroom. The bag's customizable nature allowed for the selection of a gingham print, a pattern that complements a variety of classic ensembles.

4. Pearl Earrings

If you tell me you are a preppy dresser and don’t have pearl earrings, I don’t think I could believe the former. Pearl earrings are essential for a preppy style. Pearls are the epitome of class and sophistication; a preppy outfit is incomplete without them. 

Don’t spend tons of money on pearl earrings if you don’t want to! My pearl earrings are $3 from a local boutique. People usually can’t tell the difference!

5. Complimentary Watches and Bracelets

Every girl needs some arm candy to round out their outfit. You can add a class level to your outfit if you have several staple pieces that match, such as a bangle and a watch in one metal tone (such as gold).

6. Cap-Toe Flats

First of all, ballet flats are a must for a preppy wardrobe. Find an essential pair, such as black or nude flats, and add cap-toe flats. These are very Blair Waldorf but also very classic and Parisian. The cap-toe truly polishes the outfit by adding a flair of flirtiness and girliness.

7. Sweatshirts & Tees

Channel your inner Princess Diana with an oversized graphic sweatshirt paired with athletic bottoms—anything from a pleated tennis skirt to your favorite pair of biker shorts will do. 

Both tennis graphic sweatshirts and rugby-style ones will make you feel like you’re about to head to the courts (in a chic way).

8. Athletic Skirts & Dresses

You can’t have preppy and sporty-chic without a few classic tennis skirts and dresses. Whether 

If you prefer the quintessential white pleats or want to branch out to a fun color or a different style, there is no shortage of insanely cute options for everyone. 

The best part? These can be dressed down with a sweatshirt or dressed up with a nice sweater.

9. Varsity-Style Knits & Polos

Take your preppy look from the tennis courts to boarding school with a:

• Varsity-style sweater

• Vest

• Classic polo top

• These timeless pieces make an understated statement in a calming color palette of neutrals, greens, and bluest.

25 Top Preppy Girl Outfit Ideas in 2024

1. Show Off Your Socks: The Essential Preppy Style Accessory

Long socks have become essential to the preppy look, whether crew length or knee-high. While they're often paired with loafers and babydoll shoes, we're partial to these ballet flats, which refresh the popular aesthetic.

2. Try a Graphic T-Shirt: A Preppy Style Game Changer 

If you want a more casual feel with an Indie Sleaze spin, trade your standard button-down for a graphic tee instead. This quick switch is an easy yet effective way to make your school girl's outfit stand out.

3. Add Some Edge with Combat Boots: Unlikely Preppy Style Footwear

For a twist on the schoolcore trend, Lovello suggested ditching the Mary Janes and opting for moodier footwear, like combat boots.

"I would take the plaid skirt — and make sure it's a mini — and pair it with logo designer tights and combat boots to add edge," she said.

4. Go Extra Preppy with a Tie: Channel Your Inner Nerd

"It's not schoolcore without a pleated mini skirt, knee-high socks, and a tie," Warren told us, adding that sky-high platform loafers or oxfords will elevate the look.

Alternatively, you can ditch the skirt altogether by opting for an oversized shirt and blazer combo (called lampshading).

5. Break Out the Trousers: Preppy Styles Updated Bottoms 

A wide-leg khaki pair is classic school-core attire styled with a button-down and loafers. Swap out your dress shirt for a cropped sweater to modernize this uniform.

6. Say Yes to Knits: Preppy Style's Cozy Layering Piece

Sweaters can be worn as a top or added to your outfit as an accessory. If choosing the latter, style it over a button-down or let it hang over your shoulders for some added flair.

7. Risk Being Risqué with a Bandeau Top: A Bold Preppy Move

Gonzalez Mayo shared that her ideal schoolcore outfit is preppy "but also a little risqué." Her go-to combines a matching plaid blazer and skirt set with a bandeau bra top, knee-high socks, and loafers. The result will get you the celebrity-loved bracket look with an overtone of light academia.

8. Stick with a Scheme: Preppy Style Color Palettes

Nothing feels more uniform (or like an actual uniform) than a sleek, monochromatic moment. Moody black is perfect for fall — or any time of year, for that matter. Don't be afraid to experiment with color for a dose of dopamine dressing.

9. Slip on Some Accessories: Standout Preppy Style Details

Channel your inner Blair Waldorf with a headband, or go more Do Revenge with a beret. Both are solid options that will make your schoolgirl outfit noteworthy.

10. Incorporate Personal Style: Make Preppy Your Own

Add your favorite accent to the mix once you've got your main preppy piece, such as a pleated skirt or plaid blazer. Don't shy away from color, and get creative with footwear — there are no rules here.

11. Opt for a Full Suit or Matching Set: Preppy Style Made Easy

We enjoy a pre-made, no-fuss outfit, and with a button-down shirt and tie, you'll appear ready for class. There are many ways to wear suits today, but the consensus is that less is more. Read:

• Backless

• Pantless

• Shirtless

12. Proud Monograms: A Collegiate Preppy Look

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

13. Cher Horowitz-Inspired Plaid: Preppy Styles Forever Classic Look

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

14. Vintage-y Cable Knit: Cozy Preppy Style Classics

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.

15. Cool in Crimson: A Preppy Style Color Palette

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.

16. Trouser Shorts: A Preppy Style Alternative for Warm Weather

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.

17. Sweater (Vest) Weather: A Preppy Style Layering Essential

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.

18. Preppy Prints Turned Cozy: Updating Preppy Styles for Fall

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.

19. Plaid on Plaid: Mixing Preppy Patterns

Feel free 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

20. Belts, Caps, and Bags: Preppy Style Accessories

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.

21. Gothic Peacoat: An Edgy Preppy Style Alternative

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.

22. Varsity Jacket: A Retro Preppy Style Essential

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

• Pants

23. Nautical Cardigan: The Ultimate Preppy Style Look

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.

24. Clean White Turtleneck: A Preppy Style Classic

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.

25. Updated Penny Loafers: Preppy Style Footwear That Pops

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.

Preppy Little Girls’ Clothes That Are Practical Too

Preppy Fall Favorites for Minis

Fall is upon us, and I can’t help but get excited about dressing my girls for the season. Today, I’m sharing my preppy fall favorites for minis. This list is not comprehensive; it merely represents a selection of products that have been personally used and appreciated over time and items that have garnered interest.

Before proceeding with the product recommendations, it is essential to consider the following insights gleaned from experience in purchasing children’s clothing:

Size Up for Longevity

Always size up. ALWAYS. Thou shalt not buy 4T clothing for a four-year-old. Depending on said four-year-old's stature, thou shalt buy 5T or 6T. Emma, for example, has always been high on the percentile chart. She’s four years old, and I buy a 5/6 and sometimes a 6/7, depending on the brand. 

Roll those sleeves and embrace the flowy look! Get a few years’ wear out of products and get the most of your hard-earned money.

Consider Play When Selecting Kids' Clothing

Remember the importance of play. I would love to dress my girls in gorgeous smocked dresses exclusively! And sometimes I do buy them for special occasions. But I’ve found they’re far happier when they wear comfy and seasonally appropriate clothing they like and can play in. 

Emma requests to wear a dress daily, so I look for them in knits, flannel, fleece, super-soft denim, and velour and pair them with cozy leggings or footless tights. I also give her choices at night when we pick out her outfit for the following day, and then I note what she likes best for future purchases.

Know Where to Save and Where to Invest

I buy about half of Emma and Lucy’s clothing from stores like:

• Old Navy

• Gap

• J.Crew Factory

• Carter’s

Socks, underwear, leggings, jeggings, solid basics, onesies, whatever—all the staples that typically don’t make it to the next child anyway because of the normal wear and tear that kids put on clothing. I love these brands.

Value Buys

The sales are fantastic, I know what to expect, and they always have some adorable or trendier pieces that bring some life to the girls’ wardrobe without breaking the bank. I also don’t cry if something gets destroyed or lost.

I sometimes pay for high-use products—such as waterproof Uggs (SO necessary in Chicago) and Patagonia jackets—because they hold up extraordinarily well. If I get the sizing right, we can get several years of wear out of them. They can also be passed down to Lucy, thus extending their wear even more, which saves me a lot of time and money in the long run. 

Strategic Splurges

Quality over quantity and buy nice instead of twice, if you will. Of course, this works well for me because I have two girls, and it would be a little more challenging if I had a boy and a girl! I’ll admit that I occasionally splurge on special occasion wear or things I fall in love with. (Ralph Lauren, Boden, crewcuts, Joules, Lilly Pulitzer, Janie & Jack, Patagonia, Ugg, and Vineyard Vines are my weaknesses. But I’ve been lucky enough to work with these brands over the years, so that’s been helpful. 

For any investment, though, I wait for sales and comb the internet for coupon codes. Some of my favorite super preppy—but often super pricey—companies include:

• Maisonette

• Bella Bliss

• Little English

I’m just now getting into kids' brands, including Zara, which is SO CUTE, and Hannah Andersson.

Stay Organized

Create an organizational system and keep up with it. In our first home, Emma’s closet was a 

mess. It was overflowing with clothing—some of which fit, and some didn’t. To be honest, I’m not sure why it took me so long to do something about it; I guess I was just really overwhelmed, trying to pull off being a stay-at-home mom who also works full-time from home. (It's so cute that I thought that was possible.) 

Seasonal Sorting

My friend Barbie told me I needed to invest in storage tubs or bins and label them by size and gender. (For example, 0-24 months GIRL, 2T-3T GIRL, 4T-5T GIRL… and so on.) This is such a simple concept but such a game-changer. At the end of every season, I evaluate the girls’ clothing. 

It goes into a bin if it’s in good shape but doesn’t fit. If it’s something we don’t get a lot of use out of or is showing wear, it goes into the donation bag. I just pulled out the 2T-3T GIRL bin and went shopping for Lucy. Some things are too big for her, but others are spot on and work perfectly. It’s also very sentimental! I have vivid memories of little Emma in so much of the clothing.

Buy Oxyclean

This is the stuff we use. (It’s safe to use on whites!) Before I found it, I regularly deemed many things beyond repair. I just couldn’t get the stains out. 

Smart Schoolwear

Smart, classic, and wearable – here’s how to add a touch of dress-up to your kids’ look that still works for outdoor adventures.

Dip Into Schoolwear

Don’t be afraid to borrow staples from the school uniform range. Pretty blouses, classic jumpers, and cardigans add a well-dressed vibe and look great mixed with cool skirts like this one. And because it’s schoolwear, you get all the added innovations (like non-iron shirts), so it’s super-durable and easy to wash.

Add A Touch Of Tartan

Tartan is a great way to add a preppy-smart look, whether it's a shirt or skirt. But there are a couple of rules to follow—don’t overdo it; one item is enough. Pair with neutrals (grey, black, or white) to keep the look sleek. This skirt is a skort—a skirt panel over shorts—making it brilliant for tree climbing and handstands.

Try Out A-Chino

Chinos are an easy upgrade to a well-dressed look and a great addition to a boy’s wardrobe for those moments (mainly coming up to Christmas) when he needs to add a touch of smart. These are cotton mixes, making them perfect for playtime as they’re stretchy and (thank goodness) supremely washable.

Give A Button-Up A Go

There’s something about boys in a button-up shirt that’s just adorable. Whether you choose from check, gingham, plaid, or plain, worn open over a plain tee in early autumn and, come winter, worn under a jumper, they will look brilliantly smart.

Go Cord

Timeless, durable, and classic, the cord has a moment in kidswear. It’s a great autumnal material, and this green pinafore is the perfect piece to buy now. It’s easy to layer and will look just as cute in the winter, worn over a jumper with tights and ankle boots.

Stick To Muted Colors

Kids look brilliant in bright colors, but if you want to keep the look classic, go for autumnal shades such as:

• Navy

• Deep red

• Bottle green

• Mustard yellow and rust

Bonus: These colors don’t show up dirt as much.

Get The Shoes Right

Ballet pumps, monochrome high-top trainers, plain ankle boots, and brogues are the preppy footwear of choice. For your peace of mind, our suede shoes and boots are treated to be water-repellent, meaning they’ll stay smarter for longer.

Don’t Be Afraid Of Sparkle

Glitter and sequins are too fabulous to leave out of a dressed-up look. So add:

• Sparkly trainers

• Bags

• Gloves

• Scarves

• Hair accessories

If the outfit is simple and classic, like this fabulous spotted jumpsuit, adding some sparkle won’t stop the look from being smart.

Go Collegiate

That old-school US college look of baseball jackets, cardigans with striped bands on the arm, and jumpers with contrasting trim works especially on kids. It looks cool and gives their outfits a smarter vibe.

Layer, Layer, Layer

Preppy is a very practical style trend in autumn and winter. It’s all about layering, particularly for boys. Whether it’s shirts over tees, cardis over polos, or jumpers over button-ups, layering adds detail. 

As a general rule of thumb, only have a pattern (check or stripe) on one of the layers and keep the block color neutral using the following:

• Blue

• Black

• Grey

• White

Layering means you can strip off or add on – very handy for active kids!

Color Analysis by WhatColors

WhatColors helps you find what colors to wear based on your skin tone. Finally, thanks to our patented color match technology, you can get your season based on your skin tone. Get the perfect colors based on your season. Avoid colors that are a definite no. 

Based on your skin, eye, and hair color, find the perfect nail color with our WhatColors nail color generator. Get your color analysis done within 60 seconds with WhatColors’ AI personal color analysis app. Download our app for free today on the App Store or Google Play store. 

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Do Preppy Girls Wear Jeans?

Jeans have made their way into nearly every style category, preppy included. Traditionally, jeans were a major taboo in the preppy community, mainly because they were far too casual for the classically tailored aesthetic of the look. To put it frankly, blue jeans just didn’t cut it. With today’s evolving fashions, it’s possible to find styles that achieve the polished appearance of preppy clothing while offering the comfort and versatility of denim.

Tips for Styling Jeans for a Preppy Appearance

While you can wear jeans any way you choose, there are specific techniques to remember when styling them for a preppy look. Here’s how to incorporate denim into your wardrobe without sacrificing your preppy style.

Timeless Cuts

Stick to classic, timeless cuts. For women, this means opting for skinny or straight styles. After all, boat shoes don’t pair well with bell bottoms, and a boot cut doesn’t necessarily mean duck boots.

Wash Matters

Washing your denim is very important! Classic white, black, and medium or dark blue are your best options for incorporating denim into a preppy wardrobe. 

These washes look classic and clean when paired with your favorite sweater, polo, preppy tee shirt, or button-down.

Details Make the Look

Pay attention to the details. They can make or break the look. Tears, holes, rips, and frays are the biggest offenders here, as they bring down the tailored preppy look. Stick to denim with no distressing (and so would your mother). 

A tasteful frayed hem here and there is quite acceptable. Apart from distressing, steer clear of gaudy stitching or overdone hardware. After all, you want to keep the spotlight on your pearls or KJP watch.

Your Guide to Preppy-Approved Jeans

So, what styles should you look for when shopping for jeans with your preppy outfits? Here are some excellent options to get you started:

The Basic

The key to pulling off denim as preppy is simplicity. These solid navy blue jeans from Southern Tide are perfect for pairing with bright polos and button-downs. No rips or tears and minimal fading on the front ensure you’ll look classy and tailored no matter how you style these jeans. 

We suggest pairing them with:

• A striped button-down

• A bright belt

• Jack Rogers or Sperrys

The Classic White

They say no to white jeans after Labor Day, but how could you resist such a clean and classic look? White jeans are always welcome in the preppy style, and they pair wonderfully with:

• Navy Shep Shirts

• Bright Gretchen Scott blouses

• Punchy Lilly Pulitzer Popovers

We are especially in love with this pair from Vineyard Vines. The simple details don’t steal the spotlight of your outfit, and the slightly frayed hem adds a touch of something different to your preppy style.

A Hint of Pastel

Every preppy girl loves pastels, and the bright summer days they remind us of. Pastel denim is no exception! Nothing says sweet southern style like these Ralph Lauren Pink Pony jeans paired with:

• A white blouse

• Pearls

• Jack Rogers 

• Tory Burch Millers

It has the style of a pastel chino with all the comfort and versatility of denim.

The Light Wash

During the summer months, you might want a classic pair of jeans with a lighter wash than the first pair shown. Rest assured, we’ve found the perfect pair for you. The classic slim cut of these slightly cropped jeans from J. Crew is perfect for a French tuck and will complement various body types. 

Added bonus: The side seams of these jeans have a small line of pink piping that we are in love with!

The Embellished Pair

Every girl needs a pair of party pants! We are in love with these golden polka dot-embellished jeans from Lilly Pulitzer, and we know you will be, too, as soon as you get your hands on them. If you want the most fun and preppy pair of jeans on the market, these are certainly for you. 

Pair them with gold Jack Rogers, pearls, and a white button-down (extra points if you pop the collar) for the perfect preppy party look.

For Cozy Days

A Patagonia pullover, camp socks, and Sperry duck boots sound perfect for a chilly fall or winter day! All that’s missing is a simple and comfortable pair of jeans to complete the look. This is where stretchy jegging comes into play. Soft and comfortable, these Performance Stretch Jeans from L.L. Bean are perfect for your chilly days. 

PS: the slender ankle opening will tuck perfectly into your camp socks.

We <3 Stripes

Color block stripes have long been a preppy style staple for their crisp and tailored look. These Mother jeans bring an exciting flair to classic white denim with a fun cropped cut and bold colors up and down the sides. 

The perfect nautical look is in your hands when you pair these jeans with Sperry or TorySport sneakers, a bright polo, and (of course) a corded sweater tied around your neck. You’ll also be the most preppy and stylish woman on the high seas or land.

The Cool Culotte

Old-school culottes have finally returned in style, and here at Country Club Prep, we could not be more thrilled! The vintage feel of these jeans brings back an air of classic American preppy style. Envision yourself aboard a luxurious sailboat or attending a polo match, adorned in a neck scarf gently swaying in the wind, while savoring a mint julep while wearing these jeans. 

We sure can. Pair these culottes with a Kelly green polo and tan sandals for a classic, comfortable, preppy outfit.

Polished and Professional

We know what you’re thinking: Jeans! Polished and Professional? How! Allow us to explain. It is very well possible to achieve a polished and professional preppy look sans a seersucker frock or pleated skirt. 

When paired with a preppy blouse, tailored blazer, classic pearls, and simple heels, these dark wash Hudson jeans make for a classy and fuss-free outfit, perfect for dinners or days at the office.

Classic Black

Achieving the preppy style involves pairing classic basics together for a timeless look. A pair of black jeans is a must for incorporating denim into your preppy style. You should also have a pair of layered polos, flowy blouses, a seersucker blazer, or an Oxford button-down. 

This skinny cropped cut will give the appearance of long, lean legs and is perfect for tucking into your favorite preppy riding boots.

Style Guide

Now that you know what to look for in the denim world, allow us to share some tips on styling them to their preppiest potential. Prepare yourself to get a lot of compliments; you can thank us later.

Casual Everyday

Looking for a more casual and comfortable preppy outfit for your busy life? We are here to help. When paired with basics like a striped button-down, simple flats, and gold jewelry, these simple medium-wash jeans make for an easy and on-the-go preppy outfit. 

Simple preppy style at its finest! From lunch with the ladies to football practice with the kids to busy days running errands, this outfit will keep up with you and keep you looking fashionable all at the same time.

Comfy Cozy

Did your ears perk up at the previously mentioned perfect jeans to pair with duck boots on a cold day? It’s okay; we know they did. Jeans are a must on a chilly day for their warmth and comfort, but how you style them makes all the difference. 

This may be the preppiest gal of all time, and with this guide you very well could be too. At the very first sign of a chill, I.E. when the temperature drops below 70 in the south, pair a dark wash skinny jean with camp socks, duck boots, a gingham button down, and a classic vest for a look that says preppy with no if’s, and’s, or but’s.

Preppy & Polished

Now that we have established that it is in fact very possible to look polished and preppy while still wearing blue jeans, let’s go over exactly how to do so. Remember the white, dark wash, and pastel jeans we mentioned before? 

Pair either of them with a button down oxford, flowy blouse, or striped tee, a navy or black blazer, classic pearls, and fun heels for a look that says, “Yes, I’m preppy, yes, I’m wearing blue jeans, and yes I look fabulous.” Casual Friday has never looked so preppy.

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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. Fet 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.