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What to Wear With Leggings to Make Them Actually Look Chic

05/03/2025
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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 lifelong 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

MILAN ITALY  FEBRUARY 24 A guest wears sunglasses a white jacket with black buttons a black leggings pointed shoes  a...

Edward Berthelot/Getty Images

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 skintight 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.

Mostrin Sheer Kitten Heels

Vuori AlltheFeels Daily Legging

Tone Down a Trench Coat

PARIS FRANCE  MARCH 11 A guest wears dark brown sunglasses navy blue zipped jacket light gray trench coat shiny black...

Edward Berthelot/Getty Images

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