Celebrity Style

23 Years Ago, Jennifer Aniston Was So Ahead Of Her Time

The Friends star casually pioneered the exposed-bra trend.

by Jake Viswanath
LOS ANGELES, CALIFORNIA - NOVEMBER 17: Jennifer Aniston  attends Elle Women In Hollywood 2025 at Fou...
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Jennifer Aniston has always been ahead of her time — and of course, Rachel Green, by extension. The actor influenced a huge part of Y2K fashion thanks to her breakout series Friends and her own red carpet appearances. But she’s also a low-key pioneer of today’s most beloved naked fashion trends, freeing the nip and wearing sheer looks before the terms were even invented.

In 2002, Aniston attended the Lili Claire Foundation's 5th Annual “Helping Kids Fly Higher” Benefit Gala, which was hosted by her Friends co-star Matthew Perry. That night, she casually spearheaded the exposed-bra trend over 20 years before it really took off, proving that Aniston walked so today’s style girls could run.

Jennifer’s Casual Sheer Top

Walking the red carpet at the charity gala, Aniston made naked fashion trends look effortless. She wore a completely sheer black tank top, showing off her sultry lace bra underneath. The garment featured sequined floral embroidery and scalloped detailing along the slightly cropped hem.

She paired her top with perfectly pleated black work trousers, with a wide-legged silhouette that shielded her open-toe silver sandals.

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Aniston found a way to add some winter flair in Los Angeles by carrying a silky black scarf with a fringe trim as if it were a clutch bag, wrapped into a knotted ball. In true Y2K fashion, she carried an actual handbag as well, completing her look with a matching black shoulder bag.

Aniston’s Early Freed Nip Look

A few months earlier, Aniston freed the nip — possibly without even realizing it.

During the MTV Icon special, she presented an award with Liv Tyler in a classic Y2K black tube top, featuring a jagged collar and ruched pleats. The top was just see-through enough to show that she was braless, but she strategically covered her top with her microphone to avoid MTV’s censors.

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Like her exposed-bra look, she paired her top with low-rise black trousers and went minimal with her accessories, save for an elaborate gold cuff bracelet with diamond engravings.