1999
Britney Spears in khaki pants and sneakers on a trip to Disney World in Florida, June 15, 1999.
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Image Credit: Shutterstock -
1999
Image Credit: Shutterstock Britney Spears in bootcut jeans and sandals on the streets of New York in 1999.
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1999
Image Credit: Shutterstock Britney Spears in an Abercrombie and Fitch T-shirt and chunky sneakers in Flushing, N.Y. on Aug. 28, 1999.
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2000
Image Credit: Shutterstock Britney Spears arrives at London’s Heathrow Airport in 2000.
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2002
Image Credit: Shutterstock Britney Spears wears a floral coat, distressed jeans and chunky sneakers in Paris in January 2002.
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2002
Image Credit: Shutterstock Britney Spears wears platform flip-flops and bootcut jeans in Los Angeles, October 2002.
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2002
Image Credit: Shutterstock Britney Spears wears a crop top, yoga pants and chunky sneakers in Los Angeles, Oct. 13, 2002.
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2002
Image Credit: Shutterstock Britney Spears wears sparkly pink pumps and a minidress at an online gaming tournament in Beverly Hills, Calif. in October 2002.
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2002
Image Credit: Shutterstock Britney Spears goes shopping in Paris wearing tan boots and a fur-trimmed coat in October 2002.
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2002
Image Credit: Shutterstock Britney Spears sports pink snakeskin boots in London in 2002.
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2003
Image Credit: Shutterstock Britney Spears goes shopping in Los Angeles clad in a blue velour Juicy Couture sweatsuit and chunky sneakers in February 2003.
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2003
Image Credit: Shutterstock Britney Spears wears moto boots and a miniskirt out and about in Los Angeles, Feb. 27, 2003.
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2003
Image Credit: Shutterstock Britney Spears wears boot-cut jeans with black boots and a cropped sweatshirt for a shopping trip in Los Angeles, Feb. 27, 2003.
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2003
Image Credit: Shutterstock Britney Spears wears a tube top, boot-cut jeans and brown boots in Los Angeles, March 5, 2003.
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2003
Image Credit: Shutterstock Britney Spears wears a white tank top, jeans and tan boots for an August 2003 shopping trip in Los Angeles.
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2003
Image Credit: Shutterstock Britney Spears arrives at her hotel in New York in 2003 wearing tan boots and a denim miniskirt.
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2004
Image Credit: Shutterstock Britney Spears wears youga pants and sneakers in Santa Monica, Calif. with brother Bryan on Jan. 30, 2004.
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2004
Image Credit: Shutterstock Britney Spears wears a pink turtleneck and ripped jeans out and about with brother Bryan in Los Angeles in January 2004.
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2004
Image Credit: Shutterstock Britney Spears in a plaid cap, sweater, low-rise jeans and black square-toe boots in February 2004 in California.
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2004
Image Credit: Shutterstock Britney Spears wears a track jacket, yoga pants and chunky sneakers in Los Angeles in February 2004.
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2004
Image Credit: Shutterstock Britney Spears on the beach in Los Angeles wearing Nike sneakers, denim shorts and a bikini top in April 2004.
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2004
Image Credit: Shutterstock Britney Spears wears gray sneakers with cargo pants in Beverly Hills, Calif. in April 2004.
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2004
Image Credit: Shutterstock Britney Spears wears ripped jeans and square-toe boots in Ireland in June 2004.
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2004
Image Credit: Shutterstock Britney Spears wears socks and yellow sweatpants exiting a gym in Ireland in 2004.
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2004
Image Credit: Shutterstock Britney Spears (L) with mother Lynne Spears clad in denim shorts and Ugg boots in Santa Monica, Calif. in June 2004.
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2004
Image Credit: Shutterstock Britney Spears wears a graphic T-shirt, linen pants and flip-flops with Kevin Federline in Los Angeles in June 2004.
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2004
Image Credit: Shutterstock Britney Spears (L) in a gray tank top, denim shorts and ugg boots with younger sister Jamie Lynn in Los Angeles in June 2004.
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2004
Image Credit: Shutterstock Britney Spears wears a crop top, low-slung jeans and flip-flops out and about with Kevin Federline in Los Angeles in July 2004.
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2004
Image Credit: Shutterstock Britney Spears wears a pink top, shorts and flip-flops in Santa Monica, Calif. on July 21, 2004.
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2004
Image Credit: Shutterstock Britney Spears wears a pink lace top, denim shorts and flip-flops to a nail salon in Hollywood, Calif. in July 2004.
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2004
Image Credit: Shutterstock Britney Spears wears a red skirt and flip-flops out and about with Kevin Federline in Los Angeles in August 2004.
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2004
Image Credit: Shutterstock Britney Spears wears flip-flop wedges out and about with Kevin Federline in Los Angeles in August 2004.
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2004
Image Credit: Shutterstock Britney Spears in flip-flop wedges and a striped minidress in Los Angeles, Aug. 31, 2004.
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2004
Image Credit: Shutterstock Britney Spears wears a tank top, denim skirt and flip-flop wedges with Kevin Federline and his daughter, Kori, in September 2004.
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2004
Image Credit: Shutterstock Britney Spears wears a tank top, sweatpants and chunky sneakers in Louisiana in September 2004.