Jennifer Aniston's Chicest '90s Red Carpet Trend Is Back—Here's My Favorite $125 Version

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Not many red carpet trends are easily translatable to everyday wear, but in the case of a particularly iconic '90s Jennifer Aniston outfit, it definitely can be done. At the height of her Friends fame, Aniston walked the SAG Awards red carpet wearing a slim-fit, keyhole-cutout gown. I've already been seeing keyhole cutouts everywhere in 2026, so it's safe to say the look is officially back. With the sultry slim fit of Aniston's red carpet OG, NBD's Stevie Gown ($124) is my favorite interpretation right now.

This year's SAG Awards, which have been renamed The Actor Awards, take place on Sunday, March 1, so I've been reminiscing about past fashion moments in anticipation. Who What Wear will be on the ground IRL, capturing the red carpet looks in real time, so be sure to follow us on Instagram and TikTok. In the meantime, scroll down to revisit Jennifer Aniston's 1999 dress.

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(Image credit: Getty Images)

Jennifer Aniston at the Screen Actors Guild Awards in 1999.

Shop Keyhole Cutouts for 2026

Erin Fitzpatrick
Erin Fitzpatrick
Associate Director, Fashion News

Erin got her start as a Who What Wear intern in 2011—back when the site only published a single story per day. (We have since increased that number twentyfold.) She graduated magna cum laude from USC and lives in Los Angeles. In college, she also interned at Refinery29, where she was promoted to editorial assistant and then assistant editor. After nearly three years at R29, she came back to WWW in 2015, where she is now the Associate Director of Fashion News. From the Oscars to the Met Gala, she leads the site's entire red carpet coverage strategy. She specializes in celebrity and fashion news but also enjoys writing travel features and runway reports. She frequently contributes to WWW's social accounts and has a sizable following on her personal TikTok.