There are some award show looks that set the bar for all to follow. We’ll never forget Björk’s swan dress, when Rihanna wore thousands of Swarovski crystals and not much else, nor that Jennifer Lopez’s plunging Versace dress was the reason Google Images was invented.
During the endless parade of awards shows each year, we find ourselves wondering: Who delivered ingenue energy á la Gwyneth Paltrow in her bubblegum pink Ralph Lauren dress, popped a leg like Angelina Jolie, or rocked a suit like Celine Dion?
So, we’ve decided to pay homage to some of the most legendary red carpet moments of all time with the Vogue Awards, a new series in which we attempt to answer those very questions. Demi Moore—for the second year running—is “giving Cher” in a feathered showgirl look (this one’s Gucci), while Audrey Nuna, in her gilded Thom Browne look, is capping off a breakthrough season. And, when it came to the Angelina Jolie Award for Best Slit, nobody was beating Renate Reinsve.
Here, we combed the 2026 Oscars red carpet to see who delivered the most memorable looks of the evening.
The Björk Award for Most Avant-Garde
Chloé Zhao
The Jennifer Lopez Award for Biggest Bombshell
Mikey Madison in Dior
