The indisputable Princess of Pop, Britney Spears has cemented her status as an icon in the music industry and a rare example of a once-teen idol whose celebrity status has endured the test of time. As relevant as ever, we’re taking you through all the best, worst and so-bad-it’s-good fashion moments of her style evolution.
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A pop star on the rise
Signed to Jive Records at just 15 years old in 1997, Spears was already on an industry fast-track by 1999, releasing her first studio album, with the second not far behind — both being massive global successes. Britney’s style has always been aligned with her musical sound at the time, and here she's looking like the quintessential pop princess.
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An awards show fixture
Early on in her career, already a global sensation and teen idol, Britney seemed to spend most of her time onstage, rocking costumes that usually consisted of crop tops, super low-rise pants and no shortage of sequin sparkle.
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Denim glam with Justin Timberlake
In what will no doubt live on as one of the most talked-about celebrity matching outfit moments of all time, Brit and then-boyfriend Justin Timberlake showed up for the American Music Awards in 2001 rocking this. The denim-clad duo looked as tacky as possible, but somehow — and we still don’t know how, exactly — they made this explosion of style-wrong work itself out into a right.
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From the hat to the lace inserts — and those shoes! — the fact that Britney showed up to the MTV Video Music Awards in 2002 dressed like a “sexy cop” at Halloween wasn’t as bad as the accessory choices that finished off the “look"…
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Rocking a velour tracksuit
Because can you really even call yourself a celeb from the 2000’s if you don’t have a collection of velour tracksuits?
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Wearing all the things
Who wears a fedora, bow-tie, cropped-tee, short-shorts and printed stockings, all at the same time? Britney, b*tch.
Related: JLo’s style evolution.
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Britney says “I do” to minis — and a couple marriages
In 2004, Britney married childhood friend Jason Alexander in Vegas — only to annul the union 55 hours later — getting engaged and married again to backup dancer Kevin Federline later that year. With her new plus-one almost always at her side for photo ops (if you don’t count the dogs), Britney was all smiles at the Billboard Awards, rocking yet another lacey mini-dress.
Related: The most drastic celebrity haircuts.
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Turning maternity looks
Pregnant with her first child in 2005, Brit kept her style — and self — more low-key than ever, taking a break in her whirlwind career to focus on starting a family.
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Struggling behind the scenes
From divorce to a family death, personal struggles with addiction and a rapidly deteriorating state of mental health, you’d thing the press might take the hint when things went south for Britney in 2007. Instead — predictably — the spotlight got bigger, and if her style was any reflection, the chart-topping pop princess was struggling behind the scenes.
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Rocking a silver mini-dress
It’s hard to believe with everything else she had going on, that Britney would still be expected to show up for awards shows — but in 2008, the pop princess took the stage at the MTV Video Music Awards in a silver fringed-mini and knocked it out of the park.
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Serving us a a LBD at the Teen Choice Awards
While her life may have been in chaos, Britney seemed to be turning a corner with her style in 2009, still sticking to her signature mini-dresses, but opting for more low-key looks overall.
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Making a lime-green mini work
Rocking a body-con lime-green mini dress to a Southern Style event in 2011, Britney Spears looked every bit the Femme Fatale — in line with her seventh (!!!) studio album by the same name, released later that year.
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Proving she has the X-Factor
For the second season premiere of The X Factor in 2012, Britney Spears kept her look simple, rocking a gold long-sleeved mini dress and metallic pumps for her officially launch into judging duties on the hit television show.
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Owning the colour-blocking
Rocking a colour-block bandage-style mini dress, Britney's best accessories for the premiere of Smurfs 2 in 2013 were her two adorable young sons, Sean and Jayden.
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A vision in red for the launch of a sleepwear line
Brit looked statuesque and stunning in a bold red jumpsuit for the launch of her sleepwear line in 2014. We loved the simple style and bold hue for her, and she absolutely nailed the look with a fresh face and minimal accessories.
You may also like: Everything you need to know about dying your hair blonde(r).
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She’s all shimmer and sparkle
She graced the red carpet at Elton John's AIDS Foundation Gala in 2014 in this sleek and shimmery look at no doubt turned a lot of heads. You can also credit her darker locks for all the dropped jaws that followed in her wake.
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Having fun with her look at the Teen Choice Awards
Rocking ombre-rainbow hair and a low-cut, sparkly mini-dress, Britney had her signature more-is-more style in full effect for the 2015 Teen Choice Awards.
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A knockout at the MTV Video Music Awards
In an unexpectedly edgy style choice, Britney stunned at the MTV Video Music Awards in 2016, rocking a black one-sleeved dress with a funky cut-out detail down the middle.
Related: Kylie Jenner's style evolution.
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Rocking a silver fringed mini
Everything about this look is classic Britney — and we’re here for it. Overkill fringe detail and all.
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Flaunting her figure in a red mini dress
Amid ongoing conservatorship battles, family drama and new romances, Britney showed up for a film premiere in 2019 and looked as calm and cool as ever, rocking a red one-shoulder mini dress and black pumps.