The Unexpected Leggings I'm Seeing Celebs Bring Back From the 2000s
I'm here for this Y2K redux that’s been seen on all generations from Gigi Hadid to Tracee Ellis Ross.
I’m fully prepared to admit I didn’t see this one coming: Leather leggings are back. Yes, those leather leggings—the 2000s ones you wore with an oversized sweater when you wanted to feel cute but also comfortable. Except now, it’s all in the styling. And yes, they look cooler than ever. Gigi Hadid has been wearing them in that effortless, model-off-duty way, and Tracee Ellis Ross has been styling them for the ultimate elevated comfort, and while I thought this was a trend I’d never return to, I’m happy to report I’m feeling inspired.
What I love most is how this trend keeps jumping generations. Millennials wore them first, then Gen Z rediscovered them through all of the Y2K nostalgia, and now celebrities across age groups are proving they’re more about personal style than a single era. The modern versions are sleeker, softer, and infinitely easier to dress up. Below, the best celebrity outfits, plus the leather leggings actually worth investing in.
If you like making comfort look glam, you’ll love to see how Tracee Ellis Ross styled her leather leggings. A hoodie, gold jewelry, and heeled boots made it a look worthy of a fancy dinner, yet at the end of the day, it’s still leggings and a hoodie.
My dream outfit come the truly cold days of winter will most definitely revolve around leather leggings, an extremely oversize coat, and sunglasses. The look says “no one talk to me—I’m being cozy” in the best way.
So there’s the comfort-first approach to wearing leggings, and then there’s Gigi Hadid. She styled her leggings with a bomber jacket, silver jewelry, and slicked back hair for a TV performance. On the outside, she looks daring, but on the inside, you can just tell that she’s comfortable.
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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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