Rihanna didn't hit her stride until her third studio album, 'Good Girl Gone Bad,' dropped in 2007. Up until that point the Bajan bombshell had been candy sweet, with long honey brown hair and a cookie-cutter mallrat uniform. The success of 'Umbrella' -- the lead single from the LP -- led to a major boost in sales.

Her new look, a black asymmetrical bob, led to a major boost in style cred. That year, Rihanna visited MTV's 'TRL' set and debuted her new look, rocking all-black everything -- from her shrunken vest to her skintight, acid wash jeans. It would be her first step towards an edgy persona, leaving her cutesy look behind.