What to Wear With Leggings to Make Them Actually Look Chic

Undoubtedly one of the most polarizing trends in fashion history, figuring out what to wear with leggings has been a key part of the Millennial existence. If you’re over the age of 30, the athleisure staple has likely carried you through every major milestone of your life. Thirty-somethings have lived through two once-in-a-lifetime recessions, an unprecedented global pandemic, and several housing crises…and in spite of all that, leggings have prevailed.

During high school, we wore flared versions (a.k.a. yoga pants) with North Face jackets and Ugg boots. A few years later, we traded those for ankle-hugging styles that showed off our booties and became the norm so quickly they even surpassed the omnipresent skinny jeans as the pants of choice for college-aged women. In adulthood, the critical eyes of Gen Z made us briefly question this life-long allegiance to the wardrobe staple. But then quarantine hit and, suddenly, leggings were the most-worn item in our collective closets once more.

Today, the style is just as popular as it was back in 2012—the only difference is, now we’re much better at styling them. With the rise of microtrends—see: corporate sleaze, quiet luxury, and “European summer”—today’s leggings are being worn in chicer ways than they ever have before. In fact, they’re so chic, I’d dare say even Gen Z would approve.

Ahead, read up on these and more insider-approved outfit formulas that will make 2015’s biggest trend feel so 2025.

French Girl Corpcore

The last few fashion seasons have played host to a plethora of business-casual staples that absolutely demand to be worn with a comfy pair of leggings. Fitted blazers, specifically, offer the perfect amount of structure to offset these skin-tight bottoms. Finish with a pair of slinky pumps or kitten heels for a classy take on the ’90s secretary look for date night or the office.

Courtesy of brand

Mostrin Sheer Kitten Heels

$50 $40

Amazon

Courtesy of brand
Original image by Glamour commerce writer Jenny McCoy

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Vuori AlltheFeels Daily Legging

$79

Nordstrom

$98

Vuori

Tone Down a Trench Coat

The easiest way to make a Saturday morning hangover ’fit look put-together is by popping on a trench coat with a pair of posh flats (ballet, loafers, etc.). This simple addition can make any piece of loungewear feel less “couch rot” and more “cool New York City girlie.” This rule applies to your standard black leggings, of course, but it also works with hoodies, oversized T-shirts, and baggy track pants.

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The Drop Noa Trench Coat

$50

Amazon

Courtesy of brand
Original photo from Morgan Rees testing Bombshell Sportswear Scrunch Thigh High Leggings

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Bombshell Sportswear Scrunch Thigh High Leggings

$92

Amazon

Pantaboots

Pantaboots have been a running joke since they first debuted in 2022—and honestly, fair. But when done well—say, with a crisp blazer, button-up, and necktie—the legging/footwear hybrid comes out looking surprisingly elevated. You don’t have to actually invest in a pair to pull off this look, either. Just style your best Alo leggings with a pair of sock boots for a quick-and-easy dupe.

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Reformation Louie Stretch Sock Booties

$378

Reformation

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Alo 7/8 High-Waist Airbrush Leggings

$108

Alo

“Euro Summer” Capri Pants

The return of capri pants is one that no one asked for, but everyone seems to be buying into—particularly, those who have been waiting for leggings to make a full-scale comeback. You’ll surely remember the knee-length styles of the 2010, which were commonly worn with Old Navy flip-flops and PINK-branded hoodies. Now, we’re doing them Euro-style, i.e. with a gilded chain belt, puff-sleeve blouse, and a pair of strappy sandals.

Courtesy of brand

Jeffrey Campbell Leeda Ankle Strap Sandal

$90

Nordstrom Rack

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Year of Ours Ribbed Veronica Capri Legging

$92

Revolve

’80s Influence

Yep, stirrup leggings are back. And if you’re looking for ways to style your own, I’d recommend outfit ideas that involve reaching for other fashion trends from the same era. Gloves, pumps, and an oversized leather or suede jacket (this year’s biggest outerwear trend) will underscore their retro nature, while still retaining a modern feel. In fact, this outfit idea also applies to all your favorite leggings, stirrup or not.

Courtesy of brand

Naturalizer Everly Pumps

$120 $110

Zappos

Athleta Transcend High Rise Stirrup Legging

$109 $55

Athleta

Edgy Layers

This look is truly a testament to the versatile nature of a good pair of leggings. If you’re looking for a more daring leggings outfit, consider a mash-up of funky layers. Double down on belts, slip on a pleated skirt, and finish with a sporty zip-up for a playful, Miu Miu-inspired ’fit.

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J.Crew Pleated Knee-Length Skirt

$168 $100

J.Crew

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Original image from Amanda Alvarez testing Aurola Workout Leggings

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Aurola Workout Leggings

$28

Amazon

Luxe Faux Fur

If winter 2025 taught us anything, it’s that an expensive-looking faux fur coat can make virtually anything feel stylish and cutting-edge—even your most battered pair of Lululemon tights. Add more French girl favorites (like a stretchy headband from Amazon and knee-high boots) for a leggings-forward look that feels shockingly posh. Too warm? A fuzzy vest, cardigan, or shrug over your tank top has a similar vibe without being so toasty.