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.