Pleated skirts have long been beloved by pop culture—from turn-of-the-century Wimbledon matches to turn-of-the-millennium teen films. More recently, you may have noticed a resurgence of the trend on Instagram, particularly of the sporty, tennis variety. If you follow me, you may have also noticed that I picked the past-time back up and hit the courts not once, but two weeks in a row (and yes, I have plans this weekend to make that three weeks). You can bet I dressed appropriately in a crisp new Nike skirt, and I can guarantee it's just as fun and flirty to wear as it looks. But beyond the courts? Styling pleated skirts for every day might seem cheesy at first, considering all the pop-culture characters they quickly begin to reference. However, by juxtaposing the iconic item with more modern references or elevated accessories, like the ideas below, you'll be the standout star instead.

The High Fidelity Version.
The look that arguably started the most recent pleated skirt resurgence offers one of the easiest ways to style it. Toss on a vintage graphic tee, add some chunky shoes, and start living your best life
T-SHIRT RE/Done, $50 SKIRT Aritzia, $88 NECKLACE Adina's Jewels, $125 BAG Kara, $395 SHOES Dr. Martens, $150 SUNGLASSES Crap Eyewear, $79 FACE MASK Staud, $30
The Clueless Version.
Avoid feeling overly referential to Clueless (or don't?) by pairing a pleated plaid skirt with more modern trends, like a knit bralette and a must-have It bag. 
BLAZER Mango, $40 BRALETTE Mango, $80 SKIRT Topshop, $25 BAG Staud, $295 SANDALS Porte & Paire, $260 EARRINGS Petit Moments, $35 FACE MASK Old Navy, $12
The Gossip Girl Version.
A collared shirt, whether cropped or tucked in, doesn't have to mean you're headed to Constance Billard School for Girls. While Blair Waldorf might not approve, nostalgic accessories will balance out the preppiness of the pairing.
SHIRT Notes Du Nord, $158 SKIRT Amazon, $18 SUNGLASSES Le Specs, $53 EARRINGS Mejuri, $70 BAG Zara, $60 SHOES Gucci, $320 FACE MASK Forever 21, $9
The Saved! Version.
It turns out khaki pleated skirts are not as common in pop culture (though they did have a moment in the 2004 film Saved!, which may have been missed by the teen-comedy cannon). But they feel right for 2020 when styled with a mesh top and cool-girl accessories.
TOP Ganni, $81 SKIRT Amazon, $20 SUNGLASSES Saint Laurent, $395 NECKLACE Kendra Scott, $65 SANDALS Senso, $150 BAG Source Unkown, $72 FACE MASK RE/Done, $20
The Wimbledon Version.
The simplest way to wear your pleated skirt this summer is like the Wimbledon pros—in head-to-toe white. Pile on your preppiest pieces and you'll be ready to hit the court (whether it's for a game or an Instagram, I'm not one to judge).
SWEATSHIRT Polo Ralph Lauren, $168 TOP Spiritual Gangster, $50 SKIRT Eleven by Venus Williams, $78 HAT Polo Ralph Lauren, $45 NECKLACE Petit Moments, $55 BRACELETS Petit Moments, $50 SHOES Nike, $50 FACE MASK Etsy, $50

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