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Britney Spears' Style Evolution: A Look Back At Her Most Iconic Outfits

The pop star’s red carpet looks have been daring, outrageous and oh-so-memorable through the years.
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On Assignment For HuffPost

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“Framing Britney Spears,” the documentary that offers an inside look at the #FreeBritney movement, exposes the many ways the pop icon has been mistreated by the media and those around her over the years. Spears has been under a conservatorship controlled by her father since 2008, and activists she is being held under against her will.

The documentary has given the movement even more mainstream attention, prompting new interest and concern over the case. It also served as a wake-up call to the media, fans and Justin Timberlake to finally reckon with and reevaluate the ways Spears’ life and career have gotten to this point, and the role each played in driving the narrative.

Those who grew up idolizing Britney were also brought back to the early days of her career: the hits, the ascension to stardom and, of course, the fashion.

Over the years we’ve been blessed with countless Spears style moments ― the “Baby One More Time” cover look, the Juicy sweatsuits and the denim look from the 2001 American Music Awards.

Below, 22 of Spears’ most memorable looks.

1998
L. Busacca via Getty Images
Britney Spears, then in her late teens, during a portrait session.
1998
Jeff Kravitz via Getty Images
Spears at the American Music Awards in Los Angeles.
1999
Time & Life Pictures via Getty Images
Spears at the U.S. Open in New York.
1999
Ron Wolfson via Getty Images
Spears during the filming for her "Sometimes" video in Santa Monica, California.
1999
Time & Life Pictures via Getty Images
Spears at the MTV Video Music Awards in New York.
1999
Time & Life Pictures via Getty Images
Britney Spears at a Z100 Zootopia concert.
2000
Fred Duval via Getty Images
Spears at the "Oops I Did it Again" album launch in Paris.
2000
Time & Life Pictures via Getty Images
Spears with her mother, Lynne Spears, at a Grammy party in Los Angeles.
2000
Michael Crabtree - PA Images via Getty Images
Spears at the farewell party in London for her European tour.
2000
Ron Galella, Ltd. via Getty Images
Spears at the annual Billboard Music Awards in Las Vegas.
2001
KMazur via Getty Images
Spears at rehearsals for the MTV Video Music Awards ceremony in New York.
2001
KMazur via Getty Images
Spears at the Rock in Rio music festival in Rio de Janeiro.
2001
KMazur via Getty Images
Spears at the 28th American Music Awards in Los Angeles.
2001
KMazur via Getty Images
Spears at the MTV Video Music Awards in New York.
2002
Steve Granitz via Getty Images
Spears at the Grammy awards in Los Angeles.
2002
KMazur via Getty Images
Spears at the MTV Video Music Awards in New York.
2003
Michael Caulfield Archive via Getty Images
Spears at MTV's "Bash" in Los Angeles.
2003
Frazer Harrison via Getty Images
Spears shopping in Los Angeles on Valentine's Day.
2003
Lawrence Lucier via Getty Images
Spears at the Glamour Women of the Year awards in New York.
2014
Mark Davis via Getty Images
Spears at the annual Elton John AIDS Foundation's Oscar viewing party in Los Angeles.
2015
Kevin Mazur via Getty Images
Spears at the MTV Video Music Awards in Los Angeles.
2016
Jamie McCarthy via Getty Images
Spears at the MTV Video Music Awards in New York.
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