View Gallery
48 Slides
Advertisement - Continue Reading Below
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.
Advertisement - Continue Reading Below
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.
Advertisement - Continue Reading Below
31999: Pretty in Pink
Getty ImagesBritney Spears arrives at the Shrine Auditorium in Los Angeles, California, wearing a baby pink slip dress.
Advertisement - Continue Reading Below
41999: Getting Glam
Getty ImagesBritney Spears wows in a sheer shirt at the 1999 MTV Video Music Awards.
Advertisement - Continue Reading Below
52000: Planet Hollywood
Getty ImagesBritney Spears poses at London's Planet Hollywood on November 15, 2000.
Advertisement - Continue Reading Below
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.
Advertisement - Continue Reading Below
72000: Taking Risks
Getty ImagesBritney Spears on the red carpet at the 2000 Billboard Music Awards in Las Vegas, Nevada.
Advertisement - Continue Reading Below
82000: Hollywood Glamour
Getty ImagesBritney Spears oozes old Hollywood glamour at the 42nd Annual GRAMMY Awards at the Staples Center in Los Angeles, California.
Advertisement - Continue Reading Below
92000: Making the Video
Getty ImagesAdvertisement - Continue Reading Below
102000: Teen People
Getty ImagesBritney Spears celebrates the 2nd anniversary of Teen People.
Advertisement - Continue Reading Below
112000: Lovely in Lilac
Getty ImagesBritney Spears poses at the 2000 Teen Choice Awards in Santa Monica, California.
Advertisement - Continue Reading Below
122000: Across the Pond
Getty ImagesBritney Spears launches her second album, Oops!... I Did It Again at the Eiffel Tower in Paris, France.
Advertisement - Continue Reading Below
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.
Advertisement - Continue Reading Below
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!"
Advertisement - Continue Reading Below
152002: The Grammy Awards
Getty ImagesBritney Spears poses at the 44th Annual Grammy Awards on February 27, 2002.
Advertisement - Continue Reading Below
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.
Advertisement - Continue Reading Below
172002: Little Red Dress
Getty ImagesBritney Spears rocks a low-cut red dress at the 29th Annual American Music Awards on January 9, 2002.
Advertisement - Continue Reading Below
182002: PlayStation Party
Getty ImagesBritney Spears keeps it casual for PS2 Guy Oseary's 30th Birthday Party in Beverly Hills, California.
Advertisement - Continue Reading Below
192002: Crossroads
Getty ImagesAt the Crossroads premiere with Justin Timberlake.
Advertisement - Continue Reading Below
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.

Jennifer Algoo is the Visuals Director at Harper's BAZAAR. She is a graduate of the School of Visual Arts and has previously worked at Patrick McMullan Co. as well as completing internships at Martha Stewart Weddings, Vogue and CosmoGirl! Magazine. Jennifer covers royal, celeb and art content as well as overseeing all visual assets on BAZAAR.com. When she's not obsessing over the royals you can find her attempting to solve cold cases as an armchair detective, traveling and experimenting with new recipes.
Amy Mackelden is a freelance writer, editor, and disability activist. Her bylines include Harper's BAZAAR, Nicki Swift, Cosmopolitan, Marie Claire, ELLE, The Independent, Bustle, Healthline, and HelloGiggles. She co-edited The Emma Press Anthology of Illness, and previously spent all of her money on Kylie Cosmetics.
Jacob is a Temporary Partnerships Editor at Hearst based in Queens, New York with his partner and cat Tiger. He loves learning and writing about Film and TV, Video Games, and the weird histories of unexpected subjects.
Advertisement - Continue Reading Below
Advertisement - Continue Reading Below
Advertisement - Continue Reading Below
ncG1vNJzZmivp6x7qa3RqZyrq5KWx6Kt0WeaqKVfmLKtscGroK2xX6GutbHSrWaga2VphniDj25mm6qZqbumxYysp56Zoqh6rbXFnmSipl2ltbDAzqxm