Winona Ryder's Beauty Evolution From the '80s to Now (2025)

Whether she's inspiring your '90s capsule wardrobe or your most recent Halloween costume, there's no denying that 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.

01of 25

A 2024 'Beetlejuice Beetlejuice' Event

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For the Beetlejuice Beetlejuice press tour, Ryder rocked layered bangs with a variety of updoes. Black eyeliner emphasized her eyes, while she kept the rest of her makeup muted, highlighting her poreclain complexion.

02of 25

At the "Stranger Things" Season 4 Premiere in 2022

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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 modern and refreshing.

03of 25

At the SAG Awards in 2020

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The slicked-back pony might be having a moment, but we're partial to the Hollywood veteran's tousled take, which she wore to the Annual Screen Actors Guild Awards. And while anyone can pull off this hairstyle, it's especially flattering for those with fine or thin strands. Lifted roots instantly boost volume and body.

04of 25

At the Tribeca Film Festival in 2019

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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 while the hint of sparkle in her makeup plays up the glam factor, albeit subtly.

05of 25

At the Golden Globes in 2017

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The Winona, Minnesota, native (yes, that's where she got her name!) was a knockout at the 74th Annual Golden Globes. Romantic waves, a neutral makeup palette, and flawless skin highlight her natural beauty.

06of 25

At the NYC "Paterson" Screening in 2016

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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.

07of 25

At the Sundance Film Festival in 2015

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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.

08of 25

At the Help Haiti Home Gala in 2014

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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.

09of 25

At the New York screening of "The Iceman" in 2013

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Ryder has experimented with a lot of haircuts over the years and they hit every time. Here, she opted for soft curls to complement her inverted bob. A classic red lip and all-around black eyeliner are what make this look timeless.

10of 25

At the "Frankenweenie" Premiere in 2012

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The Frankenweenie star chose a simple ponytail for the film's premiere, drawing attention to her on-point eye makeup. Follow her lead and apply shimmer to both the top and bottom lash lines, plus tons of mascara, for added drama.

11of 25

At a "Black Swan" Screening in 2010

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

12of 25

At the Premiere of "Star Trek" in 2009

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

Growing out your pixie can look awkward at times. So consider adding a hair accessory, slicking hair back, or even applying a texturizing product to reshape your style—and make it more flattering.

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At the L.A. Premiere of "Milk" in 2008

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Ryder's boyish crop featured a brow-dusting long fringe, which drew attention to her kohl-rimmed eyes. To prevent your bangs from bringing on any forehead breakouts, invest in some oil-absorbing dry shampoo.

14of 25

At the Los Angeles Film Festival in 2006

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

15of 25

At the Opening of Marc Jacobs's L.A. Boutique in 2005

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Ryder channeled modern-day Breakfast at Tiffany vibes when she wore this '60s-inspired updo at the opening of Marc Jacobs's L.A. boutique. The pearl drop earrings proved that accessories should never be overlooked.

16of 25

At the Museum Of The Moving Image Salute to Richard Gere in 2004

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The Golden Globe award-winner amped up her amber eyes with smudgy black liner and a swipe of shimmery shadow. Her mussy updo was the epitome of effortless beauty.

17of 25

At the Academy Awards in 2001

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Ryder switched up her look with long, blonde waves that seemed to pay homage to her character in the 1990 film Edward Scissorhands. "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.

18of 25

At the Academy Awards in 2000

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

19of 25

At the Cannes Film Festival in 1998

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For the Cannes Film Festival, the Girl, Interrupted star 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.

20of 25

At an Industry Event in 1997

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The Alien: Resurrection actress debuted a short crop and a bold beauty look that we're still dreaming about. Set against her fair complexion, the colors of her crimson-red lips and silvery-blue eyeshadow really pop.

21of 25

On Set of the film "Reality Bites" in 1994

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Ryder sported the original bixie haircut in the Gen X opus Reality Bites—and the look still holds up today. Her tousled layers lend movement to her straight strands, but wavy and curly hair types will find this cut flattering too.

22of 25

At the "Night on Earth" New York City Premiere in 1992

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The Dracula actress highlighted her milky complexion with blood-red lipstick and dark-dyed locks. It's a classic combination that we just can't seem to get over—and if we're being honest, we don't want to.

23of 25

At an Industry Event in 1989

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After starring in the cult classic Heathers, the starlet chopped off her locks resulting in this voluminous bob. The simple style allows her to show off her flawless complexion and full brows.

24of 25

At an Industry Event in 1985

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

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In Junior High in 1985

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At Petaluma Junior High School in California, the eighth-grader favored a spiky-haired androgynous cut influenced by the 1980s punk scene. It's visual proof that Ryder was always cool.

Winona Ryder's Beauty Evolution From the '80s to Now (2025)

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