From Hannah Montana To “Museum-Quality” Archival Looks: Charting Miley’s Fashion Evolution

“Behind every fabulous look is a four-hour fitting, and I learned that by being Hannah Montana,” Miley Cyrus jokes in her Life in Looks video, filmed to mark her June 2023 cover of British Vogue. Cyrus has used fashion as a form of expression throughout her career, and discovered in her teens how to use it as a tool to carve out her idenтιтy, separate from her Disney princess persona.

One of Miley’s breakout style moments was the Marc Jacobs mesh gown she wore with spiked hair to the Met Gala in 2023. “Even though I knew it wasn’t going to be understood or accepted by everyone, that is the point of the Met Ball: to do something that will cause conversation or possibly controversy,” Cyrus says of the defining look. “That was one of the least controversial things I did that year, was to make my hair look like a palm tree. It’s fashion!”

Miley Cyrus performing at Glastonbury. Samir Hussein

Collectable vintage fashion – specifically “museum-quality archival”, as she puts it in the film – is now a key component in Miley’s wardrobe. One of her most memorable vintage looks to date is a ’90s Jean Paul Gaultier long black dress featuring exaggerated hooped sleeves, which she wore with a directional pearl choker. Among the fashion eras she loves: Tom Ford’s Gucci, John Galliano for Dior and ’90s Gianni Versace.

“There’s a magic to vintage pieces that stand the test of time – I love all the vintage eras of fashion from ’70s Yves Saint Laurent to John Galliano for Christian Dior,” Cyrus’s stylist Bradley Kenneth, who’s been working with the star since 2015, tells Vogue. “Miley’s personal vintage collection is growing along with her style – each era takes her into a lot of different directions.”

Kenneth comments that he regularly references royals, goddesses and divas within his work: “Some of the divas I looked up to while growing up were Erykah Badu, Destiny’s Child, Grace Jones, Whitney Houston and Brandy. I’m also obsessed with ancient Egyptian queens like Neferтιтi and Cleopatra, and greek goddesses like Aphrodite and Hera.”

Cyrus’s Bangerz style circa 2013 was provocative and cartoonish, but almost a decade on she has come to appreciate more pared-back looks, too. “At one time I thought if fashion felt sophisticated it felt boring or it felt beyond my years,” she explains. The style mantra she continues to live by? “You always feel better when you know you just look sickening.”

Revisit some of the singer’s most memorable fashion looks, below.