10 ‘90s-Style Plaid Skirt Sets To Channel Your Inner Cher Horowitz

There’s nothing Clueless about this look.

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WASHINGTON, DC - JULY 14: Pop music star and Disney actress Olivia Rodrigo arrives at the White Hous...
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I can trace my personal obsession with plaid skirt sets back to my first viewing of Clueless, sometime in the late ‘90s. The cult classic spawned countless trends that would go on to define the era, from fur-lined cardigans to slinky slip dresses (which were, in fact, dresses, according to Calvin Klein, anyway). But it’s the plaid skirt set — featured prominently on the movie poster — that instantly cues up all sorts of nostalgia for the days of beepers, trips to Blockbuster, and beverages like Snapple and Fruitopia.

For those unfamiliar with the brilliance that is Clueless, Cher Horowitz (Alicia Silverstone) and Dionne Davenport (Stacey Dash) were the ultimate ‘90s queen bees. They ruled the halls of Beverly Hills High with an iron wardrobe of bright colors, vibrant patterns, and playful silhouettes. Their coordinating plaid skirt sets, in particular, made fashion history — so much so that 25 years later, Olivia Rodrigo’s 2021 White House appearance conjured up comparisons to the iconic ensembles. The “good 4 u” singer arrived in the nation’s capital last July wearing a pink vintage Chanel skirt suit.

From Cher to Olivia, a head-to-toe plaid look strikes just the right balance between timeless and trendy. It’s the perfect ‘fit for date night, whether you’re heading to a fancy dinner or a big concert. Ready to channel your own inner ‘90s starlet? You’ve come to the right place: Ahead, check out 10 different plaid skirt sets that you can start shopping right now. Your closet — even if it’s not automated by some fancy software à la Cher in the movie — will thank you.


Bouclé Plaid

Say hello to the quintessential plaid skirt set (don’t forget to snag the matching blazer). With elegant bouclé fabric, it’s impossibly chic, pairing perfectly with any type of footwear, from chunky boots to strappy heels.


Romantic Lavender

Soft and delicate, this lavender sweater set is going to become one of your new faves. Wear white sneakers for a comfy, practical look.


Dreamy Matcha

Calling all matcha lovers, this one’s for you. Why not dress like your go-to coffeehouse beverage in this light green set?


Chic Black & White

The perfect going-out ensemble doesn’t exi— wait, yes, it totally does. Layer this set over a black crop top and sheer black tights for your next night out.


Classic Tartan

This knit set features a bold, all-over plaid print with a high-rise waist and bodycon silhouette. You can easily wear it year-round, though it’s the quintessential outfit for the holiday season.


Cool & Casual

Want to run errands in style? Reach for this crisp set, which features a modern jacket (with pockets!) and a high waist skirt.


White Plaid

A neutral black and cream palette? Check. A pop of gold with those glam buttons? Check. Cher and Dionne would be so proud.


Black & Tan

When you want to be a little dressy but still cozy, this set is a must. The check design is flawless with platform sandals (as styled here) or with classic Converse sneakers.


Neutral Lines

OK, it’s technically not a set, but it basically gives the illusion of one. This longline plaid blazer can be layered over any outfit, or you can wear it alone.


Beige Houndstooth Set

Houndstooth is plaid’s close cousin — and it was also major in the ‘90s — so the pattern deserves a spot on this list. Add some chunky gold accessories for an unforgettable look.

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