1January 1999
Steve Granitz//Getty ImagesWhen Britney appeared on the scene (well, excluding her Mickey Mouse Club days, duh), she had long layers and baby-esque bangs. Also, pretty sure this is her natural color!
2January 1999
Kevin.Mazur/INACTIVE//Getty ImagesBritney's American Music Awards hair was the definition of on-trend. Crimping? Check. Beaded headband? Check. All that's missing is a butterfly clip...or two. (Or three. I loved those things, don't judge me, pls.)
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3February 1999
picture alliance//Getty ImagesThe singer modified her look ever-so-slightly towards the end of the decade with a shorter cut that is serving serious "The Rachel" vibes.
4June 1999
Brian Rasic//Getty ImagesAt the MTV European Music Awards, Britney went short with a textured bob and red lowlights (another classic late '90s/early 2000s trend, what a queen).
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5July 1999
Steve Granitz//Getty ImagesOnly one month later, thanks to what I can only assume are a few pounds of extensions, Britney was seen in concert with honey brown hair and high pigtails, naturally.
6August 1999
Barry King//Getty ImagesFinally! The golden blonde layered look I know and love her for. Her Teen Choice Awards style soon become her signature.
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7September 1999
Kevin.Mazur/INACTIVE//Getty ImagesWho else grew obsessed with super long, sleek hair after seeing Brit rock this look at the MTV Music Video Awards? Same same same.
8December 1999
Steve Granitz//Getty ImagesAnd then as soon as I committed to growing my hair out, she goes and shows up at the Billboard Music Awards with this blunt bob. Always keeping us on our toes, that Brit.
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9February 2000
Ron Wolfson//Getty ImagesThere is no more iconic Grammys look than this. Straight, sleek, icy side-part = everything.
10June 2000
New York Daily News//Getty ImagesWe're all guilty of trying to replicate this gem of a look from the singer's Oops I Did It Again era. No? Just me???
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11September 2000
Kevin.Mazur/INACTIVE//Getty ImagesWarning: Crimping your hair at home never rarely turns out looking like Britney at the MTV Music Video Awards. Doesn't mean you shouldn't try, tho! I believe in you!
12November 2000
Paul Bergen//Getty ImagesThere was no bigger fan of pigtails (or hats) than Godney. Here, she wears both at the same time on her European tour in 2000.
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13December 2000
Steve Granitz//Getty ImagesSee?? Britney LOVES a hat. Even...this Victorian-esque (??) one that she wore to the Billboard Music Awards. (Yes, good eye, it also matches her...lingerie set.)
14January 2001
KMazur//Getty ImagesBritney went more dirty than golden blonde in 2001 for her tousled Super Bowl halftime show look.
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15March 2001
Jeff Kravitz//Getty ImagesI humbly refer to this as her "Crossroads Cut" era. She wore the flipped-out, shoulder-length style while filming said iconic movie.
16June 2001
Steve Granitz//Getty ImagesBritney, is that you? She was almost unrecognizable with long platinum blonde extensions and sunglasses at a radio event.
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17July 2001
Steve Granitz//Getty ImagesFor her boyfriend-at-the-time Justin Timberlake's (!) album release party in 2001, Brit kept it simple with wavy blonde hair.
18September 2001
KMazur//Getty ImagesWhen dancing with a snake at the MTV Music Video Awards, always opt for long beach waves.
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19February 2002
KMazur//Getty ImagesWas Britney going to the Grammys or prom? Your guess is as good as mine. So. Many. Curls.
20August 2002
Mark Mainz//Getty ImagesAlas, another hat! Britney topped blunt layers and bright blonde hair with a leather Breton hat for the 2002 MTV Music Video Awards.
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