30 Photos of Britney Spears’ Evolving Style

Posted by Pamela on November 24th, 2010

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370590 02: Britney Spears, winner of Single of the Year for 'Baby One More Time', at the 1999 Teen Choice Awards in Los Angeles, CA, August 1, 1999. (Photo Brenda Chase/Online USA, Inc.)

Britney Spears has had one hell of a bumpy ride since hitting it big with her first single Baby One More Time – here is a look at her evolving style through the years – from sexy school girl to leather clad dominatrix, she has changed her look frequently over the years, even if some of her fashion choices have been questionable, others disastrous, and some unforgettable!

Here is a look at the princess of pop in all her glory, starting from her early years!

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370586 02: Teen pop sensation, Britney Spears performing at the Universal Ampitheater for her 'Baby One More Time' tour in Universal City, CA, July 31, 1999 Photo by Brenda Chase/Online USA, Inc.

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NEW YORK - SEPTEMBER 9:  Pop starlet Britney Spears attends the MTV Video Music Awards held at the Metropolitan Opera House on September 9, 1999 , in New York City, New York, USA. (Photo by Dave Hogan/Getty Images)

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LONDON - DECEMBER 05: Singer Britney Spears performs at the Smash Hits Poll Winners Party 1999 held in the London Arena,London,England on the 5th of December 1999.(Photo by Dave Hogan/Getty Images)

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Britney Spears at the 42nd Annual Grammy Awards on Wednesday 2/23 at the Staples Center in Los Angeles. Dave Hogan/Getty Images

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PHILADELPHIA - JULY 5:  American pop star Britney Spears performs on stage during her 'Oops I Did It Again' Tour on July 5, 2000 in London. (Photo by Dave Hogan/Getty Images)

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NEW YORK CITY, NEW YORK - SEPTEMBER 7:  Pop sensation Britney Spears performs during the MTV Music Video Awards on September 7, 2000 in New York City, New York, USA. (Photo by Dave Hogan/Getty Images)

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Britney Spears appears at the 28th Annual American Music Awards at the Shrine Auditorium in Los Angeles, CA on Monday, January 8, 2001 broadcast live on ABC. Photo credit: Frank Micelotta/ABC/Getty Images

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Britney Spears performing on the 2001 MTV Video Music Awards at the Metropolitan Opera House at Lincoln Center in New York City on September 6, 2001. Photo by Dave Hogan/Mission Pictures/Getty Images. **North American Sales Only**

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Britney Spears during MTV's Spankin' New Music Week on TRL at the MTV studios in New York City.  Her new album, 'Britney' was released today.  11/6/01  Photo by Scott Gries/ImageDirect

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400787 04: Musical artists Justin Timberlake (L) and girlfriend Britney Spears (R) attend the premiere of the film 'Crossroads' February 11, 2002 in Hollywood, CA. (Photo by Vince Bucci/Gety Images)

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404105 01: Singer Britney Spears attends the Australian premiere of her new film Crossroads April 18, 2002 at Fox Studios in Sydney, Australia. Crossroads is her first lead role in a movie. (Photo by Nick Laham/Getty Images)

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NEW YORK - AUGUST 29:  American pop star Britney Spears arrives at the MTv video music awards 2002 at the Radio City Music Hall on August 29, 2002 in New York. (Photo by Dave Hogan/Getty Images)

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SANTA MONICA, CA - APRIL 12:  Britney Spears and Jamie Linn Spears attends Nickelodeon's 16th Annual Kids' Choice Awards at the Barker Hangar April 12, 2003 in Santa Monica, California.  (Photo by Frank Micelotta/Getty Images)

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NEW YORK - AUGUST 28:  (U.S. TABLOIDS OUT) Singers Britney Spears(L) and Madonna perform onstage during the 2003 MTV Video Music Awards at Radio City Music Hall on August 28, 2003 in New York City.  (Photo by Frank Micelotta/Getty Images)

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NEW YORK - NOVEMBER 10:  (U.S. TABS OUT) Britney Spears appears on stage during 'Spankin' New Music Week' on MTV's Total Request Live outside at the MTV Times Square Studios November 10, 2003 in New York City.  (Photo by Scott Gries/Getty Images)

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STOCKHOLM, SWEDEN - MAY 11:  Popstar Britney Spears performs on stage during her 2004 'Onyx Hotel Tour' at Globe Arena, on May 11, 2004 in Stockholm, Sweden.  (Photo by Patrik Jonsson/Getty Images)

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NEW YORK - DECEMBER 02:  Singer Britney Spears (L) and TV anchor Diane Sawyer appear on ABC's 'Good Morning America' at The Big Apple Circus tent at Lincoln Center on December 2, 2008 in New York City.  (Photo by Bryan Bedder/Getty Images)

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Singer Britney Spears arrives at the Teen Choice 2009 Awards taping in Los Angeles, on August 9, 2009. UPI/Jim Ruymen Photo via Newscom

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33498, NEW YORK, NEW YORK - Sunday August 23, 2009. Britney Spears takes her two sons, Jayden and Sean, to see the Broadway musical The Little Mermaid . Photograph: © PacificCoastNews.com

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Britney Spears sported a style all her own as she took a shopping trip to a Los Angeles, CA are Target on September 30, 2009. Fame Pictures, Inc

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A glum looking Britney Spears heads out in Calabasas, CA with boyfriend Jason Trawick to Target on February 13, 2010 where the singer was noticed to have in place of her usual neat manicure, rough unkept nails and seemed visibly distressed.. Is her Valentine's Day not shaping up to be all that an international pop star star desires? Fame Pictures, Inc

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Britney Spears spends a Sunday afternoon in comfy clothes while she runs her errands. After getting her morning frappucino fix in Calabasas, she heads to The Dollar Book Store in Encino, CA on February 28, 2010. Is Britney learning how to bargain shop? Fame Pictures, Inc

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Britney Spears made her way on to Robertson Blvd. in Los Angeles, California on May 10, 2010 for some retail therapy. Britney did a little shopping where she tried on some over sized shirts along with accessories. After finding a fresh new outfit to wear Britney made her way over to a local restaurant for a lunch break. On Mother s Day Britney spend the day without her boys, Jayden James and Sean Preston, who she sent to Disneyland with a bodyguard and a nanny, what could she have been doing? Fame Pictures, Inc

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Singer Britney Spears had quite the sour expression as she held hands with boyfriend Jason Trawick, who is rumored to have cheated on Britney with a former assistant, while entering the Courtyard Marriott Hotel in Calabasas, CA on June 11, 2010.  Fame Pictures, Inc

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Britney Spears let her hair extensions, underwear, body parts and erratic emotions all hang out on a standard Starbucks run Thursday afternoon in Los Angeles. Showing off her body in tight and tiny shorts and a see-through tank top, Spears revealed her patterned bra and exposed her cute underwear. The singer s monstrous thigh muscles looked very well-defined, though she couldn t hide her cellulite in the LA sunshine. When her bodyguards lead her the wrong way past her car, Spears put on a display of unflattering facial expressions and growled in frustration. Once again mired in public rumors about her child-rearing and her relationship woes, Britney s bizarre behavior and frazzled appearance point to continued inner turmoil for the popstar Fame Pictures, Inc

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Singer Britney Spears leaves the house once again in an elegant dress that was likely intended to be a shirt on August 5, 2010 while out in Los Angeles on a milkshake mission to Johnny Rockets where the star not only flashed a peak of her bottom to anyone on the stairs but showed off a rather rough looking tattoo.   Fame Pictures, Inc

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44064, MAUI, HAWAII - Friday August 27, 2010. Britney Spears and her boyfriend Jason Trewick enjoy some quality time together and hit the shops Maui. Photograph: Binns, Breeden, PacificCoastNews.com

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Pop Princess Britney Spears headed into Marmalade Cafe for lunch on September 22, 2010 in Calabasas, California. Britney will be featured in next week s episode of Glee and she seems to be very excited about the event as she took to her twitter about her special show. The Hit Me Baby One More Time songstress looked great in a pink top, dark jean pants, pair of brown boots and her hair seems to have improved slightly but the different lengths constantly separate from her extensions. Fame Pictures, Inc

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A distraught looking Britney Spears attempted to hide her face from the shutterbugs on October 11, 2010 while out on a shopping spree in the Beverly Hills area of California with her trusted bodyguards by her side. As no surprise Brit was out shopping for todays outfit and accessories which she found at Envie. Spears didn't seem to be in a good mood as she ventured over to the local Starbucks for a drink with smeared make up, could she have been in tears for some reason or just another day in the life of Britney? The pop princess then made her way over to De Beers jewelry store where she showed off her extensions after pulling her hair up into a ponytail while inside but let it down as she made her exit. The pop princess has been hard at work on a new album and its rumored to be the next big thing.  Fame Pictures, Inc

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