Vanity Fair Oscars After Party: 20 Looks from the ’90s & ’00s We Still Can’t Get Over

When it comes to Oscars fashion, all eyes are usually on the red carpet. However, the Vanity Fair Oscars after-party also deserves a place on the fashion history books. After the awards ceremony wraps up, the fun begins and that is also reflected on the sartorial choices, of course. 

Since the 1st Annual Vanity Fair Oscar party took place in 1994, the event has become the place to go. Stars know it and deliver, but for us watchers, sometimes the looks fly under the radar. Even though some stars show up at the Vanity Fair Oscar party still wearing their red carpet looks (see Cameron Diaz in her Versace button-up dress below), many switch things up and opt for slightly less glamorous ensembles that make for the perfect inspiration for us commoners.  

Seeing at the ‘90s and ‘00s resurgence is currently in full swing, what better time to look back on some of the looks your might have missed? (Did you know one of Madonna’s most iconic photos was snapped during the VF Oscar party?)

Below and in no particular order, revisit 20 ‘fits celebs wore to the event during the ‘90s and ‘00s that we could still rock today without hesitation — plus a pic of 2022’s back-again it couple J.Lo and Ben Affleck smooching at the event in 2003 for good measure.

(ICYMI: for the 2022 Academy Awards, you can watch the Vanity Fair Oscar Party: livestream on Teen Vogue.)