Pleated skirts have a funny way of circling back just when you think you’ve outgrown them. But styled right, they’re far from precious or prissy…or that school uniform you’re picturing in your head right now. Whether it’s a sharp-pleated mini, a floaty midi, or a sweeping maxi, the right skirt can carry more than you’d expect—it’s all about what you pair it with (and how you wear it). In this guide, I’m breaking how to style pleated skirts at every length—dressed up, pared back, high-end, low-lift—and what to look for if you’re shopping now. Spoiler: these pleated skirt outfits can work for your new office dress code, a more casual look or that chic street style energy you’re ready to put out there. Just choose your length, then make it yours.
PLEATED MINI SKIRT
Mini Pleats, Maximum Impact
The mini pleated skirt may have a reputation—somewhere between school uniform and tennis court style —but styled right, it’s surprisingly versatile. There are many different ways to style a pleated mini skirt but this one is a classic and will easily become a wardrobe staple. Pair your favorite button-down shirt (or go the extra mile with an oversized shirt like this one) with a pleated mini. Knife pleats work best as they lay flat on the hips and are flattering on every body type. Add white socks and your favorite pair of white sneakers and you’ve got a stylish everyday look.
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High: If you’re looking to invest in the perfect white shirt, this oversized Oxford style will be your everyday go-to for years to come.
Low: This perfect khaki pleated mini skirt comes in at under $100. If you don’t already have a white shirt in your capsule wardrobe to go back to it (or a boyfriend/ husband you can steal one from), the Big Shirt from Gap is a great, inexpensive option. Their white crew socks are also easy on the wallet. These Adidas Sambas have become a staple that many people already have in their wardrobes. Its versatility makes it a popular sneaker as it pairs well with jeans or skirts and dresses. And Polo’s Chino Cap is a fashion favorite for its classic 90’s aesthetic.
PLEATED MIDI SKIRT
The midi is your everyday hero: from office chic to weekend ease.
This pleated-skirt outfit is stylish for 9 to 5 and beyond. A short sleeve cashmere crewneck, a midi skirt with a wide pleat and kitten heels are the perfect summer pairing. Whether you are back in the office full time or scheduling lunch meetings, this is a timeless way to clock in.
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High: These Miu Miu slingbacks are a super stylish addition to this look and with kitten heels they’re easy to wear throughout the day.
Low: This brushed cashmere tee has been on my radar all year and now it’s in my cart! It’s a great style to wear all year round, either on its own or layered with a jacket. And this pleated midi skirt from MM LaFleur is already in my closet! It’s such a great versatile skirt to wear to work on with a t-shirt for casual days. For a darker color, this belted skirt is another great option.
As far as skirt outfit ideas go, this one is so effortless that it’s hard to pass up. White on white is such a fresh look while the printed scarf and red sandals add a pop of color. It’s easy to throw a denim jacket over this on cooler nights or even a leather jacket into the fall months when you really need those extra layers.
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High: This oversized silk scarf from La Double J is made in Italy and has the most gorgeous foulard print. A perfect complement to this look tied around your waist or worn at other times tied to your bag or wrapped in your hair. These red sandals from Tory Burch are not only in the hottest sandal color of the summer but have the sculptural element that makes them an art form.
Low: Their are so many affordable white tanks that it’s hard to choose just one, and to be honest, you don’t need to! I like the neckline and armhole of this rib-knit tank as it’s a super flattering cut on everyone. And at this price point you can stock up on a few of them! This pleated midi is everything you want in a crisp, white skirt for this summer.
This outfit has mastered the high/ low look! A gorgeous pleated skirt with an oversized sweatshirt, high tops and a Chanel crossbody bag blends uptown chic with downtown cool in a modern, effortless way. With a sweatshirt and sneakers, this look can go to class, run errands or meet the girls for brunch. It’s as if you replaced your standard jeans with a much chicer friend.
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High: This pleated skirt from Jenni Kayne features accordion pleats and the perfect midi length. Not only does it come in ivory, but it comes seven other colors including lemon if you like a pop of bright colors. Add a designer bag like this Chanel quilted crossbody for a high-end impact.
Low: These Nike trailblazer high tops are not only wallet-friendly but work any time of year, year in and year out. And this oversized sweatshirt will become an instant favorite on heavy rotation in your wardrobe.
PLEATED MAXI SKIRT
Max-Appeal: Elevating the maxi pleated skirt for both day and night.
A pleated maxi in beautiful neutral colors with a black top to temper it is a chic way to style your look this summer. I’m a huge fan of vests and this one with a nipped in waist over the flowy, feminine skirt and high heels is an elegant look that easily transitions from day to night. Adding a standout bag and of-the-moment shoes really takes this look to an elevated place.
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High: Celine’s Ava Triumph bag comes in beautiful earthy colors that complement this outfit perfectly. And Bottega Veneta’s mesh pumps ups the style ante of any look it’s paired with.
Low: For vests that won’t break the bank, I love this black linen-blend vest from Gap. I own this one and wear it on repeat. This higher neck cut-away vest from J. Crew is super chic as is their pleated slip skirt. It not only looks more elevated than its price point, but with an elastic waist, it’s extremely comfortable too.
Styling Tips for Pleated Skirts
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Balance proportions: How to style pleated skirts is all about proportions. Pair voluminous pleated skirts with more fitted tops to maintain a balanced silhouette.
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Layer thoughtfully: In cooler weather, layer with a cropped cardigan or jacket to add dimension.
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Footwear choices: Flat sandals or classic pumps can complement the look beautifully in the spring and summer. Swap these for sneakers or tall boots into the fall and winter and you can wear your pleated skirts all year round.
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