Fiona Apple showing her fasion moments from '90s & '00s.
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Fiona Apple's 9 Best Fashion Moments Of The '90s & '00s

Her laidback approach to fashion is an inspiration.

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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.

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1997, Grammys

Though Apple didn't get a Grammy nomination until 1998, she still made a splash with her awards show debut.

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1997, MTV VMAs

The world may be bullshit, according to Apple's famous acceptance speech, but her white crochet dress definitely was not.

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1997, VH1 Vogue Fashion Awards

A layered and sheer mesh look that Euphoria stans would copy today.

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1998, Grammys

The "Female Rock Vocal Performance" winner eventually kicked off those clogs when she performed "Criminal" live on stage.

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1998, Oscars

Apple, dressed in a bright baby blue slip dress and matching hair accessories, with a fan.

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2000, Oscars

This trippy-printed green dress would make a pretty penny on Depop right now.

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2001, Grammys

Who knew Apple was a fan of the signature "naked" dress on the red carpet, too?

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2005, The Late Show With David Letterman

An oversized navy trench that's currently on our fall shopping wishlist.

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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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