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 in Gabriela Hearst
The Jennifer Lopez Award for Biggest Bombshell
Mikey Madison in Dior
The Rihanna Award for Most Naked
Zoe Saldaña in Saint Laurent
The Gwyneth Paltrow Award for Leading Lady
Jessie Buckley in Chanel
The Cate Blanchett Sustainability Award for Best Vintage or Archival Fashion
Miyako Bellizzi in spring 1999 Dior by John Galliano, from Tab Vintage
The Nicole Kidman Award for Breakout Style Star
Audrey Nuna in Thom Browne
The Cher Award for Best Showgirl Moment
Demi Moore in Gucci
The Celine Dion Award for Best Suiting
Michael B Jordan in Louis Vuitton
The Angelina Jolie Award for Best Slit
Renate Reinsve in Louis Vuitton
