Take a Break From Baggy Jeans—People Are Wearing This Throwback Staple Instead

Kendall Jenner wearing flared leggings, a sports bra, and a bolero from ALO.

(Image credit: @kendalljenner)

Like any good millennial, I spent the better part of the early aughts comfily clothed in a pair of flared leggings—or, as I knew them at the time, yoga pants. I still remember my first pair from Lululemon: long and black with a pink stripe at the waistband. I'd saved up from my babysitting gigs to buy them my sophomore year of high school. Meeting up with my friends on a Saturday afternoon, I still remember how cool I felt in my Lulus, as I called them, styling them with a pair of Ugg boots peeking out underneath.

I've come a long way in developing my sense of style in the 20 or so years since I first embraced flared leggings. In fact, I'd spent at least a decade forgoing flared pants completely, opting for skinny jeans and leggings that were tight from ankle to hip. As Gen Z continues its nostalgia-driven campaign to bring them back into the fashion conversation, I've slowly become convinced.

Though I stand by the fact that fitted workout gear is better suited for the gym (no clothes catching on machines, no stepping on hems), I've found a new place for yoga pants in my wardrobe, namely as a casual weekend staple for long walks and lounging on the couch. They're unfussy and comfortable, so I can see why the generation below me has decided to embrace them once again. Ahead, I've not only shopped out my favorite flared leggings, but I've also included outfit inspiration to help you embrace them if, like me, it'll take some convincing to get back on the wagon.

How to Wear Them

Celebrities have been styling flared leggings for everything from a night out to an early morning Pilates class. Add heels, sunglasses, and a fun statement top and you have the perfect glam look, but a matching sports bra and bolero will take you straight to the reformer.

Rihanna in flared leggings.

(Image credit: Getty Images)

A woman in leggings.

(Image credit: @discodaydream)

Diane Kurger in Paris.

(Image credit: Getty Images)

Kendall Jenner in yoga pants.

(Image credit: @kendalljenner)

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Sierra Mayhew
Fashion Editor

Sierra Mayhew is a fashion editor at Who What Wear, bringing a decade of industry experience to the editorial team. Since joining in 2021, she has made her mark by blending luxury and accessible fashion, decoding runway trends, and curating must-have shopping lists. Before joining Who What Wear, Sierra sharpened her skills at Harper's Bazaar and Elle, with bylines in Bazaar.com and collaborated with iconic brands such as Gucci and Ferragamo. A graduate of the University of Notre Dame, Sierra translates editorial expertise into viral social content, making fashion engaging for a new generation. Her unique perspective is rooted in her love for travel, music, and discovering the hidden gems that make New York City a constant source of inspiration.

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