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The 26 most daring outfits Britney Spears has ever worn

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Ever since Britney Spears hit the charts back in 1998, she's been considered not only a pop idol but a fashion icon. 

Her style risks are aplenty. She turned heads when at just 18 years old she debuted "Baby One More Time" wearing a risqué Catholic schoolgirl uniform, which now acts as a go-to Halloween costume for nostalgic '90s kids.

The singer even suggestively used a snake as an accessory for her "Slave like You" performance for the 2001 VMAs.

And who could forget her iconic double denim couples outfit she rocked in 2001 with then-boyfriend Justin Timberlake for the AMAs?

So while Spears has had her fair share of critics on the red carpet, she undoubtedly influenced a generation to embrace the crop top, proving that less really can be more.

To celebrate her 38th birthday, Insider has taken a look at the singer's most daring outfits because no one makes controversial look quite as stylish as Spears does.

See them below in chronological order.

Britney influenced a generation of girls to embrace their school uniforms and wear pink marabou scrunchies in their hair after she debuted the iconic look in the 'Baby One More Time' music video back in 1998.



Spears showed up in this feathered and sheer polka dot dress, paired with dramatic 90's eyeshadow for the 1999 MTV VMAs.



Because this 1970's-esque ensemble clearly wasn't eye-catching enough, the singer got a spray tan to match her outfit for the 2000 Billboard Music Awards.



Proof that Britney made the daring thigh-high slit a thing before the Jenners. The singer wore this risqué black dress to the 2000 MTV VMAs.



One of the few times in the early 2000s when Spears didn't show off her midriff — instead, the singer completely covered up in this turtleneck pastel prom dress for the 2000 Grammys.



During rehearsals for the 2000 Grammy Awards, Britney flaunted this skin-tight, red, embellished bodysuit.



Showing off her Southern roots, Spears danced around in cream cowboy boots with a neon pink cowboy hat and a floral sundress for her performance on 'The Today Show' in 2000.



Spears left little to the imagination with this ultra thigh-high split maroon dress at the NRJ Awards in 2000.



Britney and Justin made fashion history (and internet memes for life) when they turned up to the 2001 AMAs wearing their corresponding double denim ensembles.



Who needs a necklace when a snake makes the ultimate accessory? Spears took the ultimate risk for fashion when she slithered into the 2001 VMA's in this tribal-inspired number for her 'Slave For You' performance.



Known to be quite the fan of the newsboy cap, Britney donned this black one with a bold leather vest and mesh skirt and thigh-high stilettos for the 2002 MTV VMAs.



Britney paid tribute to her performance duet partner Aerosmith by wearing a band merchandise crop top paired with a sporty arm sleeve, metallic pants, and messy rocker-chick hair for the 2001 Superbowl halftime show.



Britney poked fun at her fame by wearing The New York Post's famous gossip column Page Six across her chest and even one of their writers, Patricia Field, on her behind for the 2003 MTV Bash.



Spears wore a pair of shrunken sports shorts with a striped halter-neck cop, showing off her famous pierced belly, for 'NFL Kickoff Live' in 2003.



Britney channeled Madonna's 'Like a Virgin' video clip when she walked out at the 2003 MTV Awards stage wearing this white bridal inspired outfit, veil and all.



Spears went for this dominatrix-looking outfit for the 2003 American Music Awards.



Britney decided to test out a new color for the NRJ Awards in 2003 when she accessorized her shimmery gold bustier dress with blue contacts.



A heavily pregnant Britney wore this pale pink baby doll dress for the Teen Choice Awards in 2006.



Britney made her performance comeback at the 2007 VMAs wearing an all-too-familiar belly-showing outfit — an embellished bikini with fishnet stockings and black stilettoed boots.



Britney was the true fashion ringleader for her 2009 'Circus' tour wearing a sequin leotard leaving little to the imagination.



Spears took to the 2011 Billboard Music Awards stage in Las Vegas wearing a BDSM-inspired outfit, which matched with duet partner Rihanna in this black leather leotard with mask and even chains.



Britney crossed to the dark side when she rocked dark brunette locks with a low cut black sparkly dress for Elton John's Oscars viewing party in 2011.



She also took the plunge with this little laser-cut shimmering dress for the 2015 MTV VMAs.



Eyes were all on Spears for the 2016 Billboard Music Awards as she slid into her medley performance wearing this red bejeweled bikini.



Britney wore this asymmetrical black dress with her long, blonde, mermaid-like locks down for the MTV VMA's in 2016.



Britney embraced the sheer trend with this long sleeve mini dress for a pre-Grammys Gala in 2017.





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