The Fiona Apple Look Book

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Recording artist Fiona Apple performs at the Venice Family Clinic Silver Circle Gala Honoring Judd Apatow at the Beverly Wilshire Four Seasons Hotel on February 28, 2011 in Beverly Hills, California. Photo: Michael Bezjian/WireImage/WireImage

Back in the late nineties, Fiona Apple was a walking embodiment of the post-grunge girl. With her head of unwashed, unruly hair and a penchant for silk slip dresses, crop tops, and baggy jeans, she always managed to look feminine, rugged, fragile, and tough all at the same time (her saucer-sized, jade-colored eyes didn't hurt, either). She was only 19 years old when she released her chart-topping debut album, Tidal; now 34 years old, the Manhattan native has traded in her baby tees for floor-sweeping skirts and lots of lace. She'll never be a fashion plate, but she'll always be a fascinating-looking individual. Enjoy a look back at her outfits over the years.