It’s been a whirlwind year for Mikey Madison, who earned her first Oscar nomination—winning for Best Actress—for her breakout role as Ani in Sean Baker’s Anora. The 26-year-old actress took home an armful of other awards this season, and hosted Saturday Night Live for the first time.

While Madison’s starring role in Anora garnered her critical acclaim and propelled her further into the spotlight, she has been acting for nearly a decade. She played Max in the television show Better Things from 2016 to 2022, and in 2019, earned the part of Sadie, a crazed Manson Family follower, in Quentin Tarantino’s Once Upon a Time…in Hollywood. Soon after, she was cast alongside Jenna Ortega, Melissa Barrera and Jack Quaid in 2022’s Scream.

Despite her relatively short time on the Hollywood stage, Madison has made a big sartorial splash. Pre-Anora fame, Madison’s red carpet looks tended towards classic silhouettes, with a few bold prints thrown into the mix. Working with stylist Jamie Mizrahi, Madison’s looks on the Anora press tour and subsequent awards season circuit showcased her evolving, unique fashion sense. She showed a preference for elegant, classic Old Hollywood gowns on the red carpet, often pairing a sleek silhouette with simple accessories and waves in her hair. In 2025 she added a designer ambassadorship to her resume, as she was named a house ambassador for Tiffany & Co. and starred in their HardWear campaign.

From her first film premiere to 2025 awards season darling, see Mikey Madison’s red carpet style evolution.