1999
Britney Spears wears a pink outfit at the 1999 Teen Choice Awards.
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Image Credit: Getty Images -
1999
Image Credit: Shutterstock Britney Spears wears a see-through duster with strappy sandals at the 1999 MTV Video Music Awards.
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2000
Image Credit: Getty Images Britney Spears wears a white halter gown and sandals at the 2000 Grammy Awards.
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2000
Image Credit: Getty Images Britney Spears wears a pink and orange look with burgundy boots at the 2000 Billboard Music Awards.
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2000
Image Credit: Getty Images Britney Spears wears a black asymmetrical dress and strappy black embellished thong sandals at the 2000 MTV Video Music Awards in New York City.
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2000
Image Credit: Shutterstock Britney Spears dons a plunging jumpsuit and sandals at the 2000 American Music Awards.
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2000
Image Credit: Getty Images Britney Spears wears strappy gold platform sandals at the My VH-1 Music Awards on November 30, 2000.
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2000
Image Credit: Shutterstock Britney Spears wears a purple fringed minidress with strappy sandals at the 2000 Teen Choice Awards.
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2001
Image Credit: Shutterstock Britney Spears wears a see-through lace minidress and kitten heels at the MTV Video Music Awards on Sept. 6, 2001.
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2001
Image Credit: Shutterstock Britney Spears wearing a denim dress alongside Justin Timberlake at the 2001 American Music Awards.
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2001
Image Credit: Getty Images Britney Spears wears a cropped bustier with low-cut pants and platform sandals at the album release party for NSYNC’s “Celebrity” in 2001.
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2002
Image Credit: Getty Images Britney SPears wears a pink dress and sandals at the 29th annual American Music Awards in 2002.
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2002
Image Credit: Getty Images Britney Spears wears a red gown and sandals at the 44th annual Grammy Awards on February 27, 2002.
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2002
Image Credit: Shutterstock Britney Spears wears a pale pink minidress over skinny jeans and coordinating boots at the “Crossroads” premiere on Feb. 11, 2002.
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2002
Image Credit: Shutterstock Britney Spears models a silver halter dress and strappy sandals at the London premiere of “Crossroads” in 2002.
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2002
Image Credit: Erik Pendzich/Shutterstock Britney Spears wears a leather look with strappy black pumps at the 2002 MTV Video Music Awards.
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2003
Image Credit: Shutterstock Britney Spears sports a patterned minidress and pale yellow butterfly-embroidered cowboy boots at the 2003 Kids’ Choice Awards.
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2003
Image Credit: Getty Images Britney Spears wears an asymmetrical black strapless dress with black pointed pumps at the 2003 Glamour Women of the Year Awards.
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2003
Image Credit: Getty Images ritney Spears wears a feather-embellished dress and strappy silver metallic sandals at the 2003 American Music Awards.
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2003
Image Credit: Getty Images Britney Spears wears a cropped tee with a mini skirt over tights and pointy black pumps at the MTV Bash at the Hollywood Palladium in Los Angeles on June 28, 2003.
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2003
Image Credit: Getty Images Britney Spears wears a purple feathered coat and jeans with peep-toe pumps while promoting her album “In the Zone” in Tokyo, Japan in 2003.
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2004
Image Credit: Judy Totton/Shutterstock Britney Spears wears a gold sparkly minidress and strappy crystal-embellished sandals at the 2004 NRJ Music Awards in Cannes, France.
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2004
Image Credit: Getty Images Britney Spears wears a black lace mini dress and strappy black sandals with husband Kevin Federline at the 2004 Billboard Music Awards on December 8, 2004.
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2006
Image Credit: Getty Images Britney Spears wears a sparkly black asymmetrical mini dress with strappy black sandals at the 2006 Grammy Nominees party in Hollywood on Feb. 6, 2006.
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2008
Image Credit: Shutterstock Britney Spears wears a sheer black bodysuit with black knee-high boots at the 2008 Bambi Awards.
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2011
Image Credit: Getty Images Britney Spears wears a black sequined look complete with platform peep-toe booties at the 2011 MTV Video Music Awards.
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2014
Image Credit: McMullan/Sipa USA Britney Spears dons a plunging black sequined gown at Elton John’s annual Oscars viewing party in Hollywood on March 2, 2014.
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2015
Image Credit: Getty Images Britney Spears wears a glittery silver and gold cut-out minidress at the 2015 MTV Video Music Awards on Aug. 30, 2015.
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2016
Image Credit: Getty Images Britney Spears wears an asymmetrical black dress with black patent Christian Louboutin pumps at the 2016 MTV Music Video Awards.
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2016
Image Credit: Shutterstock Britney Spears wears a see-through black embellished gown with black thigh-high cut-out sandals at the 2016 Billboard Music Awards.
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2017
Image Credit: Shutterstock Britney Spears wears a see-through dress and pink velvet sandals at the Clive Davis pre-Grammys party in February 2017.
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2018
Image Credit: Shutterstock Britney Spears wears a crystal-embellished dress and matching pointed pumps at the 2018 GLAAD Media Awards.
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2019
Image Credit: MEGA Britney wears a black minidress and platform sandals at the 2019 Daytime Beauty Awards with Sam Asghasri.
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2019
![Los Angeles premiere of 'Once Upon a Time In Hollywood' held at the TCL Chinese Theatre IMAX in Hollywood. 22 Jul 2019 Pictured: Britney Spears. Photo credit: Lumeimages / MEGA TheMegaAgency.com +1 888 505 6342 (Mega Agency TagID: MEGA480307_009.jpg) [Photo via Mega Agency]](https://footwearnews.com/wp-content/uploads/2021/08/MEGA480307_009.jpg?w=199)
Image Credit: MEGA Britney Spears wears a red one-shoulder dress featuring a keyhole cut-out detail and black platform sandals at the Los Angeles premiere of “Once Upon a Time In Hollywood” on July 22, 2019.