Fiona Apple's 9 Best Fashion Moments Of The '90s & '00s

Bob Berg/Hulton Archive/Getty Images Fashion Her laidback approach to fashion is an inspiration. by Maria Bobila Updated: Feb. 20, 2024 Originally Published: Sep. 11, 2020

With the '90s and Y2K making a big comeback in fashion, there's no better style icon to look to for inspiration than Fiona Apple. Her laidback approach to fashion resulted in a slew of original looks, especially on the red carpet. Ahead, we look back on her best sartorial moments from the past.

Mitchell Gerber/Corbis Entertainment/Getty Images 1997, Grammys Though Apple didn't get a Grammy nomination until 1998, she still made a splash with her awards show debut.

Evan Agostini/Hulton Archive/Getty Images 1997, MTV VMAs The world may be bullshit, according to Apple's famous acceptance speech, but her white crochet dress definitely was not.

Steve Granitz/WireImage/Getty Images 1997, VH1 Vogue Fashion Awards A layered and sheer mesh look that Euphoria stans would copy today.

Steve Azzara/Corbis Entertainment/Getty Images 1998, Grammys The "Female Rock Vocal Performance" winner eventually kicked off those clogs when she performed "Criminal" live on stage .

Steve Granitz/WireImage/Getty Images 1998, Oscars Apple, dressed in a bright baby blue slip dress and matching hair accessories, with a fan.

Steve Granitz/WireImage/Getty Images 2000, Oscars This trippy-printed green dress would make a pretty penny on Depop right now.

Michael Ochs Archives/Michael Ochs Archives/Getty Images 2001, Grammys Who knew Apple was a fan of the signature "naked" dress on the red carpet, too?

Lawrence Lucier/FilmMagic/Getty Images 2005, The Late Show With David Letterman An oversized navy trench that's currently on our fall shopping wishlist.

Jon Kopaloff/FilmMagic/Getty Images 2006, Grammys Way ahead of the puffy sleeve trend, Apple wore a romantic-style gown to the 2006 Grammys red carpet.

See more throwback fashion looks from Brandy , Christina Aguilera , and Jennifer Lopez .

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