11999: A Star on the Rise
Getty ImagesBritney Spears performs during her "Baby One More Time" tour in Universal City, California, on July 31, 1999.
21999: Hitting the Red Carpet
Getty ImagesBritney Spears hits the red carpet for the 1999 Teen Choice Awards in Los Angeles. The pop star won Single of the Year for "Baby One More Time," obviously.
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31999: Pretty in Pink
Getty ImagesBritney Spears arrives at the Shrine Auditorium in Los Angeles, California, wearing a baby pink slip dress.
41999: Getting Glam
Getty ImagesBritney Spears wows in a sheer shirt at the 1999 MTV Video Music Awards.
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52000: Planet Hollywood
Getty ImagesBritney Spears poses at London's Planet Hollywood on November 15, 2000.
62000: Like Mother, Like Daughter
Getty ImagesBritney Spears arrives at the Arista Records pre-Grammy Awards party at the Beverly Hills Hotel in California, with her mom, Lynne Spears.
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72000: Taking Risks
Getty ImagesBritney Spears on the red carpet at the 2000 Billboard Music Awards in Las Vegas, Nevada.
82000: Hollywood Glamour
Getty ImagesBritney Spears oozes old Hollywood glamour at the 42nd Annual GRAMMY Awards at the Staples Center in Los Angeles, California.
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92000: Making the Video
Getty Images 102000: Teen People
Getty ImagesBritney Spears celebrates the 2nd anniversary of Teen People.
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112000: Lovely in Lilac
Getty ImagesBritney Spears poses at the 2000 Teen Choice Awards in Santa Monica, California.
122000: Across the Pond
Getty ImagesBritney Spears launches her second album, Oops!... I Did It Again at the Eiffel Tower in Paris, France.
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132001: I'm a Slave 4 U
Getty ImagesBritney Spears performs at the 2001 MTV Video Music Awards in New York City on September 6, 2001.
142001: Double Denim
Getty ImagesBritney Spears and Justin Timberlake coordinate in matching denim outfits at the 28th American Music Awards. During a recent roundtable for The Hollywood Reporter, Timberlake said, "I confess that there was maybe a period in the '90s where I could skip over some of the outfits that were public, but the Internet will never." John Legend retorted, "Denim on denim on denim on denim that will never be forgotten!"
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152002: The Grammy Awards
Getty ImagesBritney Spears poses at the 44th Annual Grammy Awards on February 27, 2002.
162002: Head to Toe Leather
Getty ImagesBritney Spears wears a dramatic leather mini dress at the 2002 MTV Video Music Awards in New York on August 29, 2002.
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172002: Little Red Dress
Getty ImagesBritney Spears rocks a low-cut red dress at the 29th Annual American Music Awards on January 9, 2002.
182002: PlayStation Party
Getty ImagesBritney Spears keeps it casual for PS2 Guy Oseary's 30th Birthday Party in Beverly Hills, California.
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192002: Crossroads
Getty ImagesAt the Crossroads premiere with Justin Timberlake.
202003: Velour Tracksuit
Getty ImagesBritney Spears is seen shopping in Calypso at the Sunset Plaza in Hollywood on February 14, 2003. She wears a classic velour tracksuit.
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