Anna Wintour's Best Met Gala Looks Through the Years: Pics - Us Weekly

Updated on: April 29, 2026 TOP STORIES 15 Theo Wargo/FilmMagic It goes without saying that Anna Wintour is an unrivaled fashion icon. The British-American journalist worked as the chief content officer and global editorial director of Vogue for 37 years before stepping down in June 2025. Throughout her tenure with Vogue, Wintour served as a chairwoman of the Met Gala since 1995, and she’s the woman behind the coveted event’s top-secret guest list. That said, all eyes are on her when she hits the red carpet at the annual gala. Thank You! You have successfully subscribed. Through the years, Wintour’s blessed celebs and fans alike with countless designer gowns. She consistently surprises fashion lovers with unique designs, but she almost always stuns in Chanel Haute Couture as her luxury label of choice. Some iconic gowns that deserve special attention are the Christian Dior Haute Couture number she wore in 2003 and the floral beaded design she debuted in 2019. She teamed both floor-length numbers with a feathered cape jacket, proving that the duo is a classic statement worthy of accolades. Keep scrolling for Wintour’s most memorable Met Gala looks of all time: Credit: Theo Wargo/FilmMagic Looking Back at Anna Wintour's Most Memorable Met Gala Looks Through the Years: Pics It goes without saying that Anna Wintour is an unrivaled fashion icon. The British-American journalist worked as the chief content officer and global editorial director of Vogue for 37 years before stepping down in June 2025. Throughout her tenure with Vogue, Wintour served as a chairwoman of the Met Gala since 1995, and she's the woman behind the coveted event's top-secret guest list. That said, all eyes are on her when she hits the red carpet at the annual gala. Through the years, Wintour's blessed celebs and fans alike with countless designer gowns. She consistently surprises fashion lovers with unique designs, but she almost always stuns in Chanel Haute Couture as her luxury label of choice. Some iconic gowns that deserve special attention are the Christian Dior Haute Couture number she wore in 2003 and the floral beaded design she debuted in 2019. She teamed both floor-length numbers with a feathered cape jacket, proving that the duo is a classic statement worthy of accolades. Keep scrolling for Wintour's most memorable Met Gala looks of all time: Credit: Theo Wargo/FilmMagic Looking Back at Anna Wintour's Most Memorable Met Gala Looks Through the Years: Pics It goes without ...