Winona Ryder's Beauty Evolution From '90s It-Girl to On-Screen Mom

Is there any look the actress can't pull off?

Winona Ryder side-swept tousled waves and deep shimmery pink lipstick
Photo: George Pimentel/Getty Images

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.

01 of 24


Winona Ryder as a spiky-haired eighth-grader
Seth Poppel/Yearbook Library

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

02 of 24


Winona Ryder shaggy, sandy, wavy hair with bangs in 1985
Getty Images

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

03 of 24


Winona Ryder with a straight brown bixie in '89
Adam Scull/Globe Photos

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.

04 of 24


Winona Ryder fair skin with red lipstick and long, black, wavy hair
Getty Images

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

05 of 24


Winona Ryder wearing her hair in a short, layered crop
Globe Photos

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

06 of 24


Winona Ryder chic pixie, red lipstick, and silvery-blue eyeshadow
Everett Collection

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.

07 of 24


Winona Ryder red-brown piecey pixie and pink frosted lips
Tony Barson/WireImage

For the Cannes Film Festival, Ryder transformed her pixie with an auburn hue. To get her piece-y texture, work some wax or pomade — we like Kenra Professional Platinum Texturizing Taffy 13 — into your 'do.

08 of 24


Winona Ryder long pixie with headband and pink lips
Tony Barson/WireImage

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.

09 of 24


Winona Ryder loose, tousled, updo with blonde face-framing waves, a smoky eye, and pink lip gloss
Jim Smeal/WireImage

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.

10 of 24


Winona Ryder mussy updo with smudgy black liner and lip tint
Lawrence Lucier/FilmMagic

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

11 of 24


Winona Ryder '60s-inspired updo with pink lips and shimmery silver eyeshadow
J. Merritt/FilmMagic

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.

12 of 24


Winona Ryder mussy bob with eyeliner, nude lip, and choker
Jason Merritt/FilmMagic

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

13 of 24


Winona Ryder straight, feathered pixie with side-swept bangs and red-pink lipstick
Michael Germana/Globe Photos

Ryder's boyish crop featured a brow-dusting long fringe. To prevent your bangs from bringing on any forehead breakouts, invest in some handy-dandy (read: oil-absorbing) dry shampoo.

14 of 24


Winona Ryder volumized, straight crop with sparkly headband, subtle smoky eye, and lip gloss
Jeff Vespa/WireImage

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.

15 of 24


Winona Ryder loose curly updo with shimmery pink makeup
Steve Granitz/WireImage

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.

16 of 24


Winona Ryder volumized ponytail with shimmery pink dramatic eyes
©Vince Flores / AFF-USA.COM

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.

17 of 24


Winona Ryder soft curl bob with eye liner and red lipstick
Rob Kim/Getty Images

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

18 of 24


Winona Ryder long, glossy waves and red lipstick
Michael Tran/FilmMagic

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.

19 of 24


Winona Ryder long, tousled waves and lip tint
George Pimentel/Getty Images

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.

20 of 24


Winona Ryder with long tousled "rock and roll" hair, eyeliner, and red lipstick

Brent N. Clarke / FilmMagic

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.

21 of 24


Winona Ryder with side-parted loose waves and light pink-nude makeup

Steve Granitz / WireImage

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

22 of 24


Winona Ryder face-framing mussy updo with eyeliner and lip tint

Gary Gershoff / WireImage

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.

23 of 24


Winona Ryder tousled updo with eyeliner and a light pink lip

Steve Granitz / WireImage

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.

24 of 24


Winona Ryder with tousled shag haircut with bangs

Arturo Holmes / WireImage

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.

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