When Heathers hit theaters in 1988, Winona Ryder was just 17. Like her character Veronica, Ryder's eighties wardrobe consisted of many oversize blazers and menswear-inspired pieces. As Ryder grew up, starred in Edward Scissorhands, and started dating Johnny Depp, her style evolved — and she began adding leather jackets, cropped pants, and more figure-revealing dresses to her wardrobe. Since then, the actress has adopted and abandoned a bold pixie cut, dabbled in headbands, and paved the way for future troublesome starlets with some memorable outfits for court appearances. In honor of the cult classic Heathers being reinvented as an off-Broadway musical, take a look back at the star's best fashion moments.