Winona Ryder, The Olsen Twins, Jennifer Aniston and Kate Winslet may grace our weekly Best-Dressed lists and Look Of The Day columns now, but they weren't always so fashionable. Same goes for the men who were popular in the '90s: Will Smith, Mark Wahlberg, Joseph Gordon-Levitt and every boy band. While stars from TV series like "Blossom," "My So Called Life," "Dawson's Creek," "Saved by the Bell" and "Boy Meets World" ruled the small screen, their personal style left much to be desired. Grunge, polyester, flannel, neon... what were we all thinking?

To celebrate (and reminisce about) the 1990s, we're taking a look back at some of the most awesomely nerd-tastic style moments from some of our favorite stars. Who do you think has changed the most?

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  • Jennifer Aniston, 1990

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  • Jaleel White, 1990

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  • Tiffany Amber Thiessen, 1990

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  • Will Smith, 1990

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  • Courteney Cox, 1990

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  • Shannen Doherty, 1990

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  • Britney Spears, 1990s

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  • Nick Carter, 1990s

    Time & Life Pictures CORRECTION: An earlier version of this slide misidentified Nick Carter.

  • Claire Danes, 1990s

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  • Christina Applegate, 1990s

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  • Melissa Joan Hart, 1990s

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  • Drew Barrymore, 1990s

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  • Alec Baldwin and Kim Basinger, 1990s

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  • Jonathan Taylor Thomas, 1990s

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  • Jamie Foxx and James van der Beek, 1990s

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  • Parker Posey, 1990s

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  • Brad Pitt and Gwyneth Paltrow, 1990s

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  • Susan Sarandon, 1990s

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  • Winona Ryder, 1990s

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  • Luke Perry, 1990s

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  • Joseph Gordon-Levitt, 1990s

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  • Neve Campbell, 1990s

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  • Lacey Chabert, 1990s

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  • Juliette Lewis and Woody Harrelson, 1990s

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  • Jennie Garth, 1990s

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  • Diane Keaton, 1990s

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  • Natalie Portman, 1990s

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  • Ricky Martin, 1990s

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  • Matthew McConaughey, 1990s

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  • Reese Witherspoon & Ryan Phillippe, 1990s

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  • Debra Messing, 1990s

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  • Christina Ricci, 1990s

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  • Jodi Sweetin, 1991

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  • Brooke Shields, Macaulay Culkin and Laura Bundy 1991

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  • Holly Hunter, 1991

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  • Eric Bogosian and Whoopi Goldberg, 1991

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  • Cuba Gooding Jr., Jared Leto and Soleil Moon Frye, 1991

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  • Sarah Michelle Gellar, 1992

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  • Joey Lawrence and Mayim Bialik, 1992

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  • Julia Roberts, 1993

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  • Tilda Swinton, 1993

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  • Mark Wahlberg, 1993

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  • Mariah Carey, 1993

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  • Angela Bassett, 1993

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  • Mark-Paul Gosselaar, 1994

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  • Tate Donovan and Sandra Bullock, 1994

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  • Ashley Olsen, 1994

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  • Jodie Foster, 1994

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  • Rider Strong, 1994

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  • Ben Stiller, 1994

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  • Geena Davis and Renny Harlin, 1994

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