A Look Back at Britney Spears's Most Memorable Onstage Outfits

By Andrea Cheng
Updated: Aug 26, 2016 @ 6:18 pm
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When it comes to Britney Spears, we're a little overprotective of her. We've seen her grow up and out of her awkward in-between stage, from when she was not a girl, not yet a woman, to becoming the princess of pop who calls out womanizers. And even though she had a mini toxic episode, she's currently back on top, stronger than ever, with a new hit single, a soon-to-be hit album (that dropped today!), and a performance at the 2016 MTV VMA Awards. And it's not that she isn't lucky (because she totally is), but her success is built on talent and hard work—Brit Brit knows how to work b**ch.

While this particular awards show may be something of a circus, with red carpet looks and onstage outfits so ridiculous they're enough to drive you crazy, we can't wait to see what Spears will turn out, especially when she has so many iconic looks in her repertoire, including nearly nude do-you-wanna-come-over separates and a real-life python as an accessory. At the end of the day though, it's really all about Britney against the music and whatever outfit she picks, we'll follow her 'til the world ends. So for all the die-hard Britney fans out there who want a piece of her (slash would voluntarily be slaves 4 her), scroll through to see all of her most memorable onstage looks in history.

Pop quiz: How many Britney Spears song titles are in this story? (The answer: 13).

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1 of 13

Billboard Music Awards, 2016

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Only Spears can perform a mega eight-minute mash-up of all of her greatest hits in bejeweled lingerie and over-the-knee boots. 

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2 of 13

Billboard Music Awards, 2011

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Spears guest-starred during Rihanna's set at the 2011 Billboard Music Awards, complementing BadgalRiRi's racy white bodysuit with a black bondage version (with bunny ears and hand cuffs, because why not) for "S&M."

3 of 13

MTV Video Music Awards, 2003

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Spears paid homage to Madonna's bridal style for a rendition of "Like a Virgin," along with Christina Aguilera, which ultimately led to the infamous three-way kiss that went down in history as one of the most outrageous moments in MTV VMA history.

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4 of 13

NFL Kickoff Live, 2003

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Spears assumed the role of referee and took the job seriously with an inspired black-and-white striped crop top and black pants, eventually stripping down (with the help of jersey-clad backup dancers) to itty-bitty booty shorts during "I'm a Slave 4 U."

5 of 13

American Music Awards, 2002

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Spears gave her racy abs-baring, booty-baring looks a break, opting for a rather demure ruffled number for one of her sweetest hits: "I'm Not a Girl, Not Yet a Woman."

6 of 13

MTV Video Music Awards, 2001

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Arguably one of Spears's most iconic outfits. While the average human would have recoiled back in fear, Spears completed her set and belted out "I'm a Slave 4 U" with nothing but a cut-out bralet, bejeweled booty shorts, and a python. 

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7 of 13

American Music Awards, 2001

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Remember when Britney and JT twinned it up in denim? She went from that iconic look on the red carpet to another one onstage—a crazy fringed top and high-shine silver pants.

8 of 13

Michael Jackson '30th Anniversary Celebration' Concert, 2001

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Michael Jackson and Britney Spears? When you have two pop icons sharing one stage, what you get is a monumental moment in music history. Of course the only outfit worthy of that is a sheer glittery, flouncy number that refracted light at every angle.

9 of 13

Super Bowl Halftime, 2001

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The halftime show ended on Aerosmith's turf, where Spears and then-bae JT (along with his boy band N'Sync), Nelly, Mary J. Blige, and Tremors & The Earthquake Horns all performed "Walk This Way." 

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10 of 13

MTV Video Music Awards, 2000

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Cover your eyes! The Princess of Pop caused quite a stir when she performed her hit single "Oops...I Did It Again" (which also received three nominations), tearing off her conservative black suit to provocatively reveal nude second-skin separates.

11 of 13

Grammy Awards, 2000

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There were dancing robots and lightning orbs, but all of that faded into the background when Spears appeared in a cut-out red-hot jumpsuit (that perhaps foreshadowed her red latex one-piece in her "Oops... I Did It Again" music video released later that year) during "Baby One More Time."

12 of 13

MTV Music Video Awards, 1999

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As the rule-breaking student, Spears wore a midriff-baring glittery leather two-piece that would have been grounds for detention during her performance of "Baby One More Time."

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