Britney Spears’s 10 Most Memorable Looks of All Time

Rachel Krause

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When it comes to celebrities whose portfolio of past looks we love to reminisce on from time to time, Britney Spears is never too far from our minds. With over 15 years on the scene, Britney has rocked her fair share of hair and makeup, and while some were better than others, almost all of them have worked their way into “iconic” status.

We couldn’t get over the rainbow waves Britney showed off at the 2015 Teen Choice Awards—which, naturally, led us directly down memory lane. Lo, this week’s Woman Crush Wednesday is none other than the inimitable Britney Spears and her best hair and makeup over the years… and some of the most “memorable,” too. It was the ’00s, after all.

Britney Spears 1999 purple eyeshadow

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Britney made her mark at the 1999 Teen Choice Awards with this fresh-faced look, light on the neutral lip color but heavy on the purple eyeshadow and wispy bangs.

Britney Spears 2002 curly hair

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The first and last time we saw Britney with a serious head of ringlet curls, the 44th Grammys in 2002 served us a major statement look.

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And so begins Britney’s hat phase: she arrived at the “Four Feathers” premiere in 2002 sporting a stylish (for 2002, of course) black hat and a big smile.

Britney Spears 2003 VMAs

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Perhaps her most iconic look (and evening) of all time, Britney’s look was elegant but still seriously early-’00s sexy at the 2003 MTV VMAs. A sign of things to come, perhaps?

Britney Spears 2003 bob

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Who could ever forget when Brit Brit dabbled in this voluminous blonde bob at the NFL Kickoff Live in 2003, complete with bangs and red streaks? Not us.

Britney Spears 2003 straight hair

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From the looks of it, Britney was just as attached to her flat iron as we were to ours in 2003. Come on, unnaturally straight hair was the look!

Britney Spears 2006 dark hair

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Britney went super dark with her hair just before giving birth to her second son, Jayden James, in 2006. Unlike the deep brown hair color, that pregnancy glow is all natural.

Britney Spears 2008 wavy hair

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Britney returned to her blonde roots at the 2008 MTV VMAs once again with these crimped waves.

Britney Spears 2012 bangs

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Britney’s look at the “X Factor” season finale in 2012 involved the perfect blowout, heavy-handed black liner, and what we eventually learned were clip-on bangs.

Britney Spears 2015 rainbow hair

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We’re all about Britney’s latest look—long, mermaid-y waves in ombré pastel colors are totally current, and the style and color are both amazing on her.