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.