The One Preppy Separate That Can Elevate All Your Spring Staples

Controversial take coming in hot: No other piece of clothing reflects this period in fashion quite like pleated skirts. Although it's easy to pass this off as a silly little skirt trend, it has surpassed being solely associated with adolescents' school uniforms and apparel worn on the tennis court. Pleated skirts have played a pivotal part in defining some of the most popular fashion aesthetics in the past year, including geek-chic fashion, tenniscore, and even the quiet luxury movement. But that's not the only reason these skirts have become a cultural phenomenon in their own right. We've also seen them into some of the most celebrated runway collections in recent seasons.
One could argue that Miu Miu's S/S 22 collection ushered in the return of the pleated miniskirt thanks to its viral khaki micro minis. Since then, we've seen the skirt silhouette continuously reinvented on the runway and in real life. The latter has particularly proven how versatile this skirt trend can be, as we've seen the style set remove its formerly preppy connotations through creative styling. No longer are pleated skirts limited to the tennis court. They've become the secret to making everyday staples feel a bit more polished. But you don't just have to take our word for it.
Ahead, we've compiled 11 pleated-skirt outfit ideas to show the various ways fashion people have been wearing them. Plus, we rounded up the best pleated skirts to shop at every price point with styling tips. Trust us when we say these outfits will no longer make you associate pleated skirts with school uniforms.
Plaid Pleated Miniskirt + T-Shirt + Oversize Leather Jacket + Sneakers
Contrary to popular belief, you can get a tad edgier with how you embrace this skirt silhouette. Try styling it with an oversize leather jacket, a T-shirt, sneakers, and rimless sunglasses. The look will be sporty and spicy at the same time.
Pleated Miniskirt + Cropped Tank Top + Sneakers
Clearly, leaning into the sporty aesthetic is an obvious way to style the pleated miniskirt. But you can make it feel more stylish by taking inspiration from the look above. Pair an athletic pleated skirt with a cropped tank top, a stretchy headband, sunglasses, and a trendy pair of sneakers.
Even if you're not on the court, this headband will keep your flyaways in check.
Pleated Miniskirt + Blouson Jacket + Loafers
You can tap into the sporty aesthetic without looking like you've just stepped off the tennis court. The key is to style this pleated miniskirt with polished items, such as an oversize blouson jacket, socks with loafers, and a quilted shoulder bag.
Although we're impartial to black, these loafers do happen to come in four other colors.
Pleated Miniskirt + Cardigan + Socks + Slingbacks + Shoulder Bag
If you're uninterested in attaining the Sporty Spice aesthetic but live for geek-chic fashion, the outfit above is right up your alley. Styling a cardigan with a matching pleated skirt and slingback heels will always earn you brownie points with the teachers.
Warning: You won't want to take this cardigan off because it's so cozy.
Plaid Pleated Miniskirt + Sweater + Peacoat + Moto Boots
Don't want your pleated skirt to read too schoolgirl coded? Pair a plaid skirt with a contrasting peacoat, an oversize bag, and moto boots. It will strike the perfect balance between formal and casual.
The bold hardware on this bag will provide the perfect contrast to your plaid miniskirt.
Pleated Miniskirt + Matching T-Shirt + Belt + Thong Sandals
Are you not into printed skirts? Go monochrome with your ensemble by pairing your favorite T-shirt with a pleated miniskirt in a matching shade. It's arguably the easiest way to make this staple feel a bit more elevated this spring.
Pleated Miniskirt + Button-Down Shirt + Blazer + Sneakers + Shoulder Bag
Have you ever seen a miniskirt look so professional? Probably not. When styled with a button-down shirt, sneakers, and a trendy shoulder bag, this outfit is living proof that pleated skirts work for all purposes.
Pinstripe Pleated Miniskirt + Matching Button-Down Shirt + Ballet Flats + Quilted Shoulder Bag
One of the most effortless ways to elevate your button-down shirt this spring is to style it with a matching pleated miniskirt. Finish off the look with a pair of ballet flats and a quilted shoulder bag, and you'll be the embodiment of elegance.
Add a quilted bag to your look for a quintessentially posh ensemble.
Pleated Miniskirt + Turtleneck + Cardigan + Belt + Cowboy Boots + Snakeskin Bag
Who said you had to get all matchy-matchy with your look? Sure, we love how well a turtleneck pairs with a pleated mini, but it's even better when it's contrasted with a pair of cowboy boots and a snakeskin shoulder bag.
Pleated Miniskirt + Cropped Polo Shirt + Vintage Bag + Retro Sneakers
If you can't possibly imagine wearing cowboy boots with a pleated miniskirt, then go for a more "traditional" pairing with a twist. With a cropped polo, a vintage shoulder bag, and retro kicks, you'll make this skirt stand out without having to take too many style risks.
We love a polo with a cropped hemline, especially one that's likely to break the dress code.
Pleated Miniskirt + Sweater-Vest + Loafers + Bowler Bag
When in doubt, you can't go wrong with styling a pleated skirt with other preppy essentials—a navy-blue sweater-vest, socks, chunky loafers, and a bowler bag. It's a failproof formula for making any ensemble look fabulous this spring.
Jasmine Fox-Suliaman is a freelance writer and editor living in New York City. What began as a pastime (blogging on Tumblr) transformed into a lifelong passion for unveiling the connection between fashion and culture on the internet and in real life. Over the last decade, she's melded her extensive edit and social background to various on-staff positions at Who What Wear, MyDomaine, and Byrdie. More recently, she’s become a freelance contributor to other publications including Vogue, Editorialist, and The Cut. Off the clock, you can find her clutching her cell phone as she's constantly scrolling through TikTok and The RealReal, in search of the next cool thing.
-
10 Who What Wear Editors, 64 Spring Buys—Inside Our Seasonal Mood Boards
Everything inspiring our wardrobes this season.
By Anna LaPlaca
-
Every Cool Fashion Person I Know Is Wearing This Retro-Preppy Top
The perfect piece to add to your spring wardrobe.
By Judith Jones
-
I'm Calling It: These Celeb-Backed Shoe Styles Are Going to Be Everywhere This Spring
Get ready.
By Nikki Chwatt
-
From Prada to COS—Here's Everything I Packed and Wore for Milan Fashion Week
A full breakdown.
By Eliza Huber
-
The 30 Items That Will Define Style This Spring
From Prada to Phoebe Philo.
By Eliza Huber
-
I Already Have an Elevated Closet, But If I Were to Start Over, I'd Go for These 5 Staples
Effortless outfit ideas ahead.
By Jennifer Camp Forbes
-
These 5 Inspiring Outfits Are Proof You Can Easily Merge Classic and Trendy Styles
Trust me, you're going to want to re-create these looks.
By Jennifer Camp Forbes
-
The 2025 It Girl's Wardrobe: 9 Highly Specific Brands and Buys They're All Wearing
From handbags to jeans to jewelry.
By Anna LaPlaca