Transformation

Nobody could call Nicole Richie boring. Ever since making her debut on The Simple Life with crayon-bright extensions, she's been Hollywood's beauty maverick. "She takes a lot of risks," hairstylist Andy LeCompte has said. The hairstylist gave Richie her style-setting Bonnie and Clyde bob that meshed flawlessly with her 60's inspired makeup. "She has a modern Twiggy feel," said makeup artist Byron Williams. "Dramatic eyes and soft lips." These days, Richie has a new career as a jewelry designer for House of Harlow 1960, and long earth-mama locks with her signature fringe. As LeCompte has said: "She loves to hide one eye behind the bangs."

1992: The 11-year-old adopted daughter of Lionel Richie looked sweet in a curly updo.