1993: Courtney Love: From baby dolls to silk dresses, punk icon Courtney Love often rocked feminine but grunge looks.
1990: Madonna: Always reinventing herself for each era, in 1990 for her Blonde Ambition Tour the "Queen of Pop" wore the now-famous bra designed by John Paul Gaultier.
1995: Jennifer Aniston: Sporting one of the most emulated hairstyles of the '90s, both Jennifer Aniston's off-screen and on-screen.
1988: Cindy Crawford: Part of the original troupe of '80s and '90s supermodels, Cindy Crawford was on the cover of every important magazine.