Britney Spears Most Memorable Music Video Looks The Hollywood Reporter
“…Baby One More Time”

Spears burst into the music scene in 1999, making a big impression with her Catholic school girl-inspired outfit and pigtails in the music video for her first single, "…Baby One More Time."
“Circus”

The pop princess staged a major comeback in 2008 with the release of "Circus" (the same name as her album). She played a ringleader in sparkling black shorts, boots and a top hat.
“(You Drive Me) Crazy”

In August 1999, Spears scored her third consecutive top 10 hit on the Billboard charts with "(You Drive Me) Crazy." In the music video, she danced her way into our hearts, wearing a shiny green crop top and black pants.
“Everytime”

The music video for the 2004 pop ballad showed that sometimes less is more, with Spears wearing a simple white button-up throughout most of the emotional clip.
“I’m A Slave 4 U”

Spears took a mature turn in the music video for "I'm A Slave 4 U," directed by Francis Lawrence, which showed the singer dancing in a sauna and wearing a hot pink bralet and a matching pink undergarment over her low-rise metallic flares.
“Me Against The Music”

Spears teamed up with Madonna for the 2003 dance hit, sporting a black suit, white tank top, a latex hat, and a PVC collar and tie in the music video.
“Oops!… I Did It Again”

Spears turned heads in the now iconic red, plastic catsuit in the Mars-themed video released in 2000.
“‘Til The World Ends”

In her 2012 hit music video, the mom-of-two avoids asteroids in an orange and red netted body suit with large crystals, a corset belt and over-the-knee black boots.
“Toxic”

There were several memorable costumes from the Joseph Kahn-directed video, but it was the hundreds of hand-glued crystals all over Spears' body that had everyone talking.
“Work Bitch”

Spears sported a custom Michael Schmidt mesh bikini with Swarovski crystal embellishments, styled by B. Akerlund, in the 2013 video.
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