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.
Getty / Ron Wolfson
At Malibu wearing a white turtleneck crop top and baggy pants.
Getty / KMazur
At the 2000 MTV Video Music Awards wearing a crop top that says “Control Freak” on it.
Getty / Jeffrey Mayer
At the 2001 American Music Awards wearing matching denim outfits with Justin Timberlake.
Getty / Dave Hogan
Posing in front of the Eiffel Tower wearing a bandana top and jeans.
Getty / Kevin Kane
At the 2001 MTV Video Music Awards holding a python wearing a green crop top and hot pants.
Getty / UK Press
At a party in London wearing a sheer purple cutout top with matching pants and shoes.
Getty / Steve Granitz
Performing in a black lace-up crop top and blue snakeskin pants.
Getty / Frazer Harrison
Leaving a store wearing a low-rise Juicy Couture tracksuit.
Getty / KMazur
Performing in a cutout crop top and studded pants.
Getty / Mark Mainz
Wearing a ruffled minidress with a newsboy hat and boots.
Getty / Mark Mainz
Styling a halterneck top with low-rise jeans.
Getty / Steve Granitz
Wearing a dress over jeans at the Crossroads premiere.
Getty / KMazur
Wearing a lace duster with her bra peeking out at the 2000 Billboard Music Awards.
Getty / KMazur
Wearing a gorgeous white gown and fuzzy shawl at the 2000 Grammy Awards.
Getty / Kevin.Mazur/INACTIVE
Styling a sparkly crop top with feather-trimmed pants at a Grammy party in 2000.
Getty / Kevin.Mazur/INACTIVE
Wearing a flame-print crop top and pants while performing on stage.
Getty / Christina Radish
Wearing low-rise pants with a barely-there top at an event.
Getty / Jo Hale
Wearing a tie-dye set with chunky sneakers while performing in Paris.
