Winona Ryder's Beauty Evolution From the '80s to Now

Whether she's inspiring Hailey Bieber's wardrobe — or your most recent Halloween costume — Winona Ryder has got covetable style. Over the course of her 30-plus-year career, the actress has nailed every beauty look imaginable, whether it be on the silver screen, the red carpet, or out with then-fiancé, Johnny Depp. From her iconic pixie cuts to her glam-grunge makeup, we're embarking on a retrospective of Ryder's beauty evolution over the years.

Keep scrolling for 24 of her most memorable looks to date.

1985

The spiky-haired eighth-grader was mistaken for a boy by her classmates at Petaluma Junior High School in California.

1985

A naturally blond Ryder launched her career with teen drama Lucas. Her face-framing bob, with its shaggy texture and volume, was '80s perfection.

1989

After starring in cult classic Heathers, Ryder chopped off her locks resulting in this hybrid bixie cut. The simple style allows her to show off her flawless complexion and full brows.

1992

The Dracula actress highlighted her milky complexion with blood-red lipstick and dark-dyed locks.

1994

Ryder sported the perfect tousled shag in the Gen X opus Reality Bites.

1997

The Alien: Resurrection star debuted a short crop and a bold beauty look that was both minimalist and maximalist. Set against her fair complexion, the colors of her glam red lips and silvery-blue eyeshadow really pop.

2000

Sometimes all it takes is a little accessorizing to up the glam factor. Case in point: Ryder's pixie complete with plus headband, which she wore to the Academy Awards.

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.

2004

The Golden Globe award-winner amped up her amber eyes with smudgy black liner and a swipe of shimmery shadow.

2005

Ryder channeled modern-day Breakfast at Tiffany vibes when she wore this '60s-inspired updo at the opening of L.A.'s Marc Jacobs boutique. The pearl drop earrings and lacy LBD seal the deal.

2006

The A Scanner Darkly star wore her chin-length bob in easy curls. The best part about this tousled style? The messier, the better.

2009

For the premiere of Star Trek, Ryder sported a space-age sparkling headband, smoky eye, and glossy lip. The look was out of this world.

2010

Looking better than ever, Ryder made the scene at a Black Swan screening with a soft, curly updo. Her shimmery pink makeup kept with the romantic aesthetic.

2012

Ryder chose a simple ponytail for the premiere of Frankenweenie, leaving the attention on her on-point eye makeup. Follow her lead and apply shimmer to both the top and bottom lash lines for added drama.

2013

Ryder opted for soft curls to complement her lob. A classic red lip and all-around black liner are what make this look timeless.

2014

The actress's long glossy mane stayed true to her brunette roots. To get her casual-cool waves, make sure to rotate your curling wand away from your face.

2015

Ryder looked fresh-faced and fabulous with au natural makeup and loosely done hair as she stepped out at the Experimenter premiere during the Sundance Film Festival.

2016

The silver screen star looked very rock-and-roll as she attended Jim Jarmusch's Paterson screening at New York City's Landmark Sunshine Cinema. With her long, tousled hair, smudgy eye makeup, and leather jacket, she is the embodiment of downtown street style.

2017

Ryder was a knockout at the 74th Annual Golden Globes. Romantic waves, a neutral makeup palette, and flawless skin highlight her natural beauty.

2019

At the 25th anniversary screening of Reality Bites during the Tribeca Film Festival, Ryder paid homage to the '90s with her glam-grunge aesthetic. The loose, face-framing updo is effortlessly cool.

2020

The slicked-back pony might be having a moment, but we're partial to Ryder's tousled take, which she wore to the Annual Screen Actors Guild Awards. Its undone finish softens her look while retaining some edge.

2022

At Netflix's Stranger Things Season 4 premiere, Joyce Byers, we mean, Ryder, makes the '80s shag fashionable again. By incorporating soft layers and texture, this updated iteration of the traditionally choppy style feels refreshing and modern.

ncG1vNJzZmivp6x7qrrSrbClnV6YvK57wp6jnpqinsG6e9OrmKerlqS%2Frq3Toqanq1%2Bstq%2B7zZpkq7GUmr%2B0ecKhmKefmaO0brjOqKKs