Popsugar Fashion Celebrity Fashion Britney Spears's Best 2000s Style Moments No One Did Early 2000s Fashion Quite Like Britney Spears 11 June 2021 by Nikita Charuza Image Source: Getty / Steve Granitz 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. Related: Meet the Designer Behind All of the Chunky 2000s Rings You've Been Seeing Everywhere Image Source: Getty / Ron Wolfson At Malibu wearing a white turtleneck crop top and baggy trousers. 1 / 18 Image Source: Getty / KMazur At the 2000 MTV Video Music Awards wearing a crop top that says "Control Freak" on it. 2 / 18 Image Source: Getty / Jeffrey Mayer At the 2001 American Music Awards wearing matching denim outfits with Justin Timberlake. 3 / 18 Image Source: Getty / Dave Hogan Posing in front of the Eiffel Tower wearing a bandana top and jeans. 4 / 18 Image Source: Getty / Kevin Kane At the 2001 MTV Video Music Awards holding a python wearing a green crop top and short shorts. 5 / 18 Image Source: Getty / UK Press At a party in London wearing a sheer purple cutout top with matching trousers and shoes. 6 / 18 Image Source: Getty / Steve Granitz Performing in a black lace-up crop top and blue snakeskin trousers. 7 / 18 Image Source: Getty / Frazer Harrison Leaving a store wearing a low-rise Juicy Couture tracksuit. 8 / 18 Image Source: Getty / KMazur Performing in a cutout crop top and studded trousers. 9 / 18 Image Source: Getty / Mark Mainz Wearing a ruffled minidress with a newsboy hat and boots. 10 / 18 Image Source: Getty / Mark Mainz Styling a halterneck top with low-rise jeans. 11 / 18 Image Source: Getty / Steve Granitz Wearing a dress over jeans at the Crossroads premiere. 12 / 18 Image Source: Getty / KMazur Wearing a lace duster with her bra peeking out at the 2000 Billboard Music Awards. 13 / 18 Image Source: Getty / KMazur Wearing a gorgeous white gown and fuzzy shawl at the 2000 Grammy Awards. 14 / 18 Image Source: Getty / Kevin.Mazur/INACTIVE Styling a sparkly crop top with feather-trimmed trousers at a Grammy party in 2000. 15 / 18 Image Source: Getty / Kevin.Mazur/INACTIVE Wearing a flame-print crop top and trousers while performing on stage. 16 / 18 Image Source: Getty / Christina Radish Wearing low-rise trousers with a barely-there top at an event. 17 / 18 Image Source: Getty / Jo Hale Wearing a tie-dye set with chunky sneakers while performing in Paris. 18 / 18 Celebrity FashionThe 2000sNostalgiaCelebrity Street StyleRed CarpetBritney Spears