Billie Eilish’s 20 Most Important Outfits of All Time

Amid a sea of Britney reincarnations (Tate McRae, Addison Rae, Madison Beer, the list goes on), one pop starlet has broken through by playing against type: Billie Eilish crashed the music scene as a tender teen, yet a fully formed artist, making music from her bedroom with her brother and eschewing all conventional ideas of how a pop star should look and act. The surprise wasn’t that she found fans. The music was great, and emo girls have long had a place at the table. The surprise was that she found so, so many. Her albums hit the top of the charts, her songs won Oscars, she landed the cover of Vogue.

Under the megawatt glare of the spotlight, Eilish made the bold choice to spend the first part of her career covering her body in oversized clothing to avoid scrutiny about her size one way or the other, opting for label-forward prints and bright hairstyles. As she grew and matured, she began to embrace her shape bit by bit and experimented with more tailored pieces, but you’ll never see her in the bodysuit other singers seem to wear as their onstage uniform or the cocktail dresses her fellow celebrities trot out for events. She is only, ever, Billie Eilish.

To see her evolution over the years, take a look back at 20 of her most interesting and iconic looks!

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Self-styled at the 2024 Golden GlobesIn true Gen Z style, Eilish pulled this outfit together piece by piece in a personal way, choosing the khaki Willy Chavarria skirt because she liked that it looked like shorts, finding the Mary Jane shoes at a thrift store, and adding the ribbon from a gift.

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In Chanel at the 2024 OscarsA more tailored, tweed version of her Golden Globes look, this is the prim and proper librarian style done right. A bit dark academia, not too revealing, feminine without being girly…it’s miles away from where Eilish started but still feels like a genuine expression of her style at this moment, if not a bit more buttoned-up than usual to go with the project she was there to support (Barbie).