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Style Evolution: Britney Spears

01/09/2010 07:19 | Updated 22 May 2015

It's been a rocky road for the pop princess, but she has come a long way since the days of Hit Me Baby One More Time. From head to toe denim and velour tracksuits to Atelier Versace, Britney has worn it all. See how her sense of fashion has changed since her days as a teen popstar.

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Style Evolution - Britney Spears

From the girl-next-door (who just happened to be an ex-Mouseketeer) to a bald isn't beautiful mother of two, Britney Spears' decade in the spotlight has been a rocky road. But with her sixth successful studio album Circus and world tour under her belt, the Princess of Pop is back on track.

Style Evolution - Britney Spears

In 1998, before she crashed onto the pop scene singing "Hit Me Baby One More Time" in a school girl's uniform, Britney Jean Spears was a fresh faced teen from Kentwood, La., with a wardrobe to match.

Style Evolution - Britney Spears

At the First Annual Teen Choice Awards in 1999, the 17-year-old Spears already knew how to stand out in a crowd - except, in those days, she did it by wearing mirrored pants in the bright L.A. sun.

Style Evolution - Britney Spears

What a difference a day makes. For her second major awards ceremony, MTV's 1999 VMAs show, Britney ditched the bubblegum look in favor of a red-hot ensemble by funky designer Todd Oldham.

Style Evolution - Britney Spears

Remember the days when Spears hinted that she would remain a virgin until she married? There was little doubt that she was hinting at something else by the time she was 18 and showed up at the 27th Annual American Music Awards in a navel-baring jumpsuit.

Style Evolution - Britney Spears

For the 42nd Annual Grammy Awards in 2000, Brit may have brought up her neckline, but her Old Hollywood screen-siren dress did little to cover up her curves.

Style Evolution - Britney Spears

Is she a refugee from Haight-Ashbury? Or trying out for a role in "Shaft"? Who knows. But whatever she was channeling at the 2000 Billboard Music Awards, Britney's electric kool aid get-up is one of her most unforgivable fashion crimes ever.

Style Evolution - Britney Spears

Nothing says I Love You like matching head-to-toe denim. A year after Britney and fellow Mousketeer Justin Timberlake went public about their romance, the duo showed up at the 2001 American Music Awards looking like they'd morphed into each other.

Style Evolution - Britney Spears

From fully covered in denim to barely draped in lace, Britney showed off a mega-smile and a killer bod at the 2001 MTV Video Music Awards.

Style Evolution - Britney Spears

For the premiere of her first film Crossroads in 2002, Britney Spears picked this is it outer-wear or is it underwear slip and jeans combo. Like the outfit, the movie was instantly forgettable.

Style Evolution - Britney Spears

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