It's rare for anyone to maintain an edgy "It" girl title for more than a few years, but Chloë Sevigny has kept her avant-garde indie status for nearly two decades. She first turned heads in the mid-nineties when she started modeling, worked at Sassy magazine, and landed an Independent Spirit Award for her role in Harmony Korine's controversial film Kids. A decade (and several artsy movies) later, she cemented her mainstream appeal a role on HBO's popular show Big Love. Meanwhile, she's kept a strong toehold in the high-fashion world, dressing in top-tier designers like Versace, Chanel, and Valentino at red-carpet events; she also designs a line for Opening Ceremony and recently reprised her role as a face of Miu Miu. Enjoy her scrappy, unconventional take on glamour through the years in our slideshow.