Rihanna: My Style Timeline

01 of 05

AUGUST 2006

AUGUST 2006
Dimitrios Kambouris/WireImage

As her career was taking off, Rihanna maintained a down-to-earth, innocent look with natural waves as she arrived at the 2006 MTV Video Music Awards.

02 of 05

NOVEMBER 2006

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Tony Barson/WireImage

The “S.O.S” singer livened things up – letting her hair go extremely curly and long – for the MTV European Music Awards in Copenhagen.

03 of 05

MARCH 2007

MARCH 2007
Jeff Kravitz/FilmMagic

Deciding her old image was “girlie and boring” the singer showed up to the Nickelodeon Kids’ Choice Awards in L.A. with a new edgy asymmetrical haircut and smoky eyes, which she calls her “bad girl look.”

04 of 05

JUNE 2007

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Steve Granitz/WireImage

Loving her short bob (“I couldn’t wait to cut my hair, I was so anxious,” she told PEOPLE), Rihanna adds bangs and a serious pose at the MTV Movie Awards.

05 of 05

AUGUST 2007

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Flynet

Though preparing for a “new look for the fall,” which will be softer and more mellow, Rihanna maintained her favorite style – a short-cropped bob and smoky makeup – for the Running Wide Open fundraising event at the California Speedway.

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