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Britney Spears's Best 2000s Style Moments

No One Did Early 2000s Fashion Quite Like Britney Spears

Y2K fashion is back whether you like it or not, and one person who was the queen of early-aughts fashion is Britney Spears. Some of her most iconic fashion moments happened during this time. We're talking about that infamous matching denim outfits both she and then-boyfriend Justin Timberlake wore to the 2001 American Music Awards, the sexy set she wore to the 2001 VMAs while holding a python around her neck, and, of course, plenty of street style moments that are a blast from the past.

As low-rise jeans and chunky jewellery make a major comeback, it's fascinating to see how Britney handled the decade's biggest trends. The "Oops!...I Did it Again" and "...Baby One More Time" was a fan of crop tops, super low-rise jeans, and velour tracksuits. (Hello, Juicy Couture!) Ahead, take a peek back in time to Britney's most stylish 2000s fashion moments.

Image Source: Getty / Steve Granitz

At Malibu wearing a white turtleneck crop top and baggy trousers.

Image Source: Getty / Ron Wolfson

At the 2000 MTV Video Music Awards wearing a crop top that says "Control Freak" on it.

Image Source: Getty / KMazur

At the 2001 American Music Awards wearing matching denim outfits with Justin Timberlake.

Image Source: Getty / Jeffrey Mayer

Posing in front of the Eiffel Tower wearing a bandana top and jeans.

Image Source: Getty / Dave Hogan

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At the 2001 MTV Video Music Awards holding a python wearing a green crop top and short shorts.

Image Source: Getty / Kevin Kane

At a party in London wearing a sheer purple cutout top with matching trousers and shoes.

Image Source: Getty / UK Press

Performing in a black lace-up crop top and blue snakeskin trousers.

Image Source: Getty / Steve Granitz

Leaving a store wearing a low-rise Juicy Couture tracksuit.

Performing in a cutout crop top and studded trousers.

Image Source: Getty / KMazur

Wearing a ruffled minidress with a newsboy hat and boots.

Image Source: Getty / Mark Mainz

Styling a halterneck top with low-rise jeans.

Image Source: Getty / Mark Mainz

Wearing a dress over jeans at the Crossroads premiere.

Image Source: Getty / Steve Granitz

Wearing a lace duster with her bra peeking out at the 2000 Billboard Music Awards.

Image Source: Getty / KMazur

Wearing a gorgeous white gown and fuzzy shawl at the 2000 Grammy Awards.

Image Source: Getty / KMazur

Styling a sparkly crop top with feather-trimmed trousers at a Grammy party in 2000.

Wearing a flame-print crop top and trousers while performing on stage.

Wearing low-rise trousers with a barely-there top at an event.

Wearing a tie-dye set with chunky sneakers while performing in Paris.

Image Source: Getty / Jo Hale

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