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.
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March 24, 2012 Performing in Atlantic City, New Jersey. Photo: Bill McCay/2012 Bill McCay
February 28, 2011 Performing at the Venice Family Silver Circle Gala in Beverly Hills, California. Photo: Michael Bezjian/2011 WireImage
September 10, 2009 With Jonathan Ames at HBO's Bored to Death premiere. Photo: Barry Brecheisen/2009 Getty Images
August 14, 2007 Performing in New York City. Photo: Scott Wintrow/2007 Getty Images
October 29, 2006 Performing at the Vegoose Music Festival in Las Vegas, Nevada. Photo: Jason Merritt
June 19, 2006 Performing in Las Vegas, Nevada. Photo: Denise Truscello
February 20, 2006 Performing in Omaha, Nebraska. Photo: Jason Squires
February 8, 2006 At the 48th annual Grammy Awards. Photo: Jon Kopaloff
Circa 2006Photo: Andrew Brusso/? Corbis. All Rights Reserved.
Circa 2006Photo: Andrew Brusso/? Corbis. All Rights Reserved.
November 25, 2005 Performing in San Franscisco, California. Photo: Tim Mosenfelder/2005 Tim Mosenfelder
October 11, 2005 Outside The Late Show with David Letterman. Photo: Lawrence Lucier
September 20, 2005 Performing in New York City. Photo: Derek Storm
March 14, 2005 At The Creative Coalitions 2005 Capitol Hill Spotlight Awards in Washington D.C. Photo: Jeff Snyder
February 8, 2004 At a Grammy Awards party in Los Angeles, California. Photo: J. Vespa
April 24, 2003 At the Richard Tyler show at Mercedes-Benz Shows LA.
Photo: J. Vespa
February 21, 2001 At the 43rd annual Grammy Awards. Photo: SGranitz
March 26, 2000 At the 72nd annual Academy Awards. Photo: SGranitz
December 8, 1999 With Paul Thomas Anderson at the Magnolia premiere in Los Angeles, California. Photo: LUCY NICHOLSON
November 30, 1999Photo: Peter Freed/? Corbis. All Rights Reserved.
September 9, 1999 Performing at KROQ's Almost Acoustic X-Mas in Los Angeles, California. Photo: Jeff Kravitz
June 17, 1998 At the Out of Sight premiere in Los Angeles, California. Photo: SGranitz
June 2, 1998 At the A Perfect Murder premiere. Photo: Gregory Pace/? Corbis. All Rights Reserved.
March 23, 1998 With Madonna at the 70th annual Academy Awards. Photo: SGranitz
February 25, 1998 At the 40th annual Grammy Awards. Photo: KMazur
Circa 1998Photo: Pablo Serrano/? Corbis. All Rights Reserved.
October 24, 1997 At the Vogue Fashion Awards. Photo: SGranitz
September 4, 1997 At the MTV Video Music Awards. Photo: Terry McGinnis
July 24, 1997Photo: John Atashian/? Corbis. All Rights Reserved.
June 13, 1997 Performing at Live 105.3's BFD
Photo: Tim Mosenfelder/2004 Tim Mosenfelder
June 1, 1997Photo: John Atashian/? Corbis. All Rights Reserved.
February 26, 1997 At the 39th annual Grammy Awards. Photo: Mitchell Gerber/? Corbis. All Rights Reserved.
Circa 1997Photo: Simon Ritter
December 13, 1996Photo: Jim Steinfeldt
September 1, 1996Photo: Terry Doyle/? Corbis. All Rights Reserved.
September 1, 1996Photo: Terry Doyle/? Corbis. All Rights Reserved.