How to Style Pleated Skirts for Fall, Inspired by Celebrities and Street Style

One of the most beloved, traditional back-to-school clothing items is the pleated skirt. For many, a pleated skirt is the foundation of a school uniform, such as the one worn by Britney Spears in the iconic “...Baby One More Time” music video or seen in numerous TV shows and movies, including Clueless and Gossip Girl. Pleated skirts have been worn by bookworms, cheerleaders, cool girls, and punk rockers both IRL and onscreen, and whether they’re mini-length, midis, or maxis, there’s just something about the pleated skirt that screams back-to-school and fall vibes.

But how do you style the pleated skirt to elevate it from the typical uniform look, or resist the urge to look like you’re doing a Blair Waldorf or Cher Horowitz cosplay? Pleated skirts can be worn so many ways: preppy, punky, vintage-inspired, sleek and modern, you name it. Stars like Olivia Rodrigo and Taylor Swift have embraced the pleats, as have designers like Miu Miu. (Remember the micro-mini Miu Miu pleated skirt that was everywhere for a while?)

If you are in for a pleated skirt fall, feel free to get creative when styling; have fun with the preppy vibes of a plaid skirt and Mary Janes, toughen it up with boots or classic Converse sneakers, or try a boho spin with an off-the-shoulder sweater. Think of a pleated skirt like a pair of jeans, or a foundational piece that you can style any way you want, no matter your personal preference or aesthetic.

Perhaps you found a pleated skirt at the thrift store and are curious about how to style it, or maybe you're in the uniform crowd and looking for fun ways to dress up that ubiquitous pleated skirt. Ahead, learn how to style pleated skirts for fall (in 6 easy ways!) with some street style inspo and a handful of our fave skirt options for any occasion.

It’s natural to veer in a preppier direction with a pleated skirt, given its instant association with school days and study halls. Lean in with traditional prep pieces like sweater vests, rugby sweaters, cardigans, and varsity jackets, and style your skirt with cute white ankle socks and a pair of loafers for an authentically studious look. Classic plaid and rich colors, such as burgundy, emerald, gold, and brown, set the tone for fall.

Bombas

Vintage Stripes Half Calf 4-Pack Socks

Pleated skirts can easily go in a more rock ‘n roll direction, which is why they’re a fave of musicians like Olivia Rodrigo. Add a vintage-inspired band tee or graphic tee and some chunky loafers or boots, and voilà! You can opt to keep it subtle, or if you want to really give it your all, add some chipped red or black nail polish and a leather jacket.

G.H. Bass

Whitney Super Lug Sole Penny Loafer

Amazon

Womens Oversized Leather Jackets

Because pleated skirts are also worn for tennis and cheerleading, they can be dressed down for a sporty, just-off-the-court vibe with a polo shirt, oversized cropped hoodie, some sweat socks, and a pair of sneakers. Add a baseball cap and casual crossbody bag for a cute and comfy weekend look. (Bonus points if your skirt is actually a skort!)

Nike

Essentials Stretch Crop Polo

AWUXINE

Quilted Tote Bag Quilted Puffer Crossbody Bag

A pleated skirt suit is so cute — just ask Sabrina Carpenter, who stole our hearts with this charcoal gray suit at a Dior Homme show. Have fun with the suiting look and channel your inner Blair Waldorf for a sweet, coquettish school or work outfit. This formula works best for formal occasions, but it's not limited to that; you can also dress down your co-ord pieces for day-to-day use and even break up the monochrome with a bright sweater or tights.

WAYF

Darby Plaid Pleated Miniskirt

Warm up on chilly fall days with a midi or maxi pleated skirt paired with a slouchy or chunky sweater and a pair of high leather boots, like the trendy but totally timeless Frye Campus boots. Coziness is unique to everyone, so it can look like multiple layers, a big sweater, your go-to bomber, a thin scarf, or just a zipped-up jacket to keep you warm and toasty.

Free People

Frankie Cable Sweater

H&M

Rib-Knit Off-the-Shoulder Top

Get creative with your layering abilities and pop a pleated skirt over your favorite pair of pants. The pleats of the skirt are an easy way to add more texture and visual interest to an outfit, and you can have fun playing with color, pattern, and fabric combinations.

Collina Strada

Brown Lawn Skirt Cargo Pants

Zara

Pinstripe Skirt Pants

Take your pick of pleats: mini, maxi, midi, sporty, or sweet! You'll be amazed at how many ways you can style a simple pleated midi or knee-length skirt.