The spiky-haired 8th grader was mistaken for a boy by her classmates at Petaluma Junior High School in California.
A naturally blond Ryder launched her career with teen drama Lucas.
She starred in cult classic Heathers rocking a classic bob.
The Dracula actress highlighted her milky complexion with blood-red lipstick and dark-dyed locks.
Ryder sported the perfect tousled shag in the Gen X opus Reality Bites.
The Alien: Resurrection star debuted a short crop-the better to showcase her glam red lips and silvery shadow.
For the Cannes Film Festival, Ryder transformed her pixie with a soft, dark blond hue.
She got glam in a single step for the Academy Awards with a plush headband.
Ryder switched up her look with long waves. "She has always been cast as the young woman with the pixie, and at this point in her career, she wanted a more adult look," her stylist Philip Carreon of L.A.'s Estilo Salon told InStyle.
She amped up her amber eyes with smudgy black liner and a swipe of shimmery shadow.
She chose a modern take on a '60s updo for the opening of L.A.'s Marc Jacobs boutique.
The A Scanner Darkly star wore her chin-length bob in easy curls.
Her boyish crop featured brow-dusting long fringe.
For the premiere of Star Trek, Ryder sported a space-age sparkling headband.
Looking better than ever, Ryder made the scene at a Black Swan screening with a soft, curly updo.
Ryder chose a simple ponytail for the premiere of Frankenweenie.
The actress debuts long hair, staying true to her brunette roots.
Actress Winona Ryder looked fresh-faced and fabulous with au naturel makeup and loosely done hair as she stepped out at the Experimenter premiere during the Sundance Film Festival in Park City, Utah.
1985
The spiky-haired 8th grader was mistaken for a boy by her classmates at Petaluma Junior High School in California.
1992
The Dracula actress highlighted her milky complexion with blood-red lipstick and dark-dyed locks.
1997
The Alien: Resurrection star debuted a short crop-the better to showcase her glam red lips and silvery shadow.
2001
Ryder switched up her look with long waves. "She has always been cast as the young woman with the pixie, and at this point in her career, she wanted a more adult look," her stylist Philip Carreon of L.A.'s Estilo Salon told InStyle.
2010
Looking better than ever, Ryder made the scene at a Black Swan screening with a soft, curly updo.
