Since she gained popularity as Paris Hilton’s mischievous sidekick on The Simple Life back in 2003, Nicole Richie’s style has come a long away. One of Rachel Zoe’s early clients, she spearheaded the millennium’s boho-chic fad with red-carpet headscarves and vintage numbers — and since then has made a statement with LA-cool-mom ensembles and lavender hair. In addition to designing her clothing brand House of Harlow 1960, Richie has maintained a television presence along the way, with a stint on Fashion Star and her own web series #Candidly Nicole. Click through our slideshow to see her style evolution through the years.