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.
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A 2024 'Beetlejuice Beetlejuice' Event
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.
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At the "Stranger Things" Season 4 Premiere in 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 modern and refreshing.
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At the SAG Awards in 2020
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.
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At the Tribeca Film Festival in 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 while the hint of sparkle in her makeup plays up the glam factor, albeit subtly.
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At the Golden Globes in 2017
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.
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At the NYC "Paterson" Screening in 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.
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At the Sundance Film Festival in 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.
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At the Help Haiti Home Gala in 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.
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At the New York screening of "The Iceman" in 2013
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.
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At the "Frankenweenie" Premiere in 2012
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.
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At a "Black Swan" Screening in 2010
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.
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At the Premiere of "Star Trek" in 2009
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
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.
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At the Los Angeles Film Festival in 2006
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.
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At the Opening of Marc Jacobs's L.A. Boutique in 2005
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.
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At the Museum Of The Moving Image Salute to Richard Gere in 2004
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.
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At the Academy Awards in 2001
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.
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At the Academy Awards in 2000
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.
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At the Cannes Film Festival in 1998
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.
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At an Industry Event in 1997
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.
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On Set of the film "Reality Bites" in 1994
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.
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At the "Night on Earth" New York City Premiere in 1992
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.
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At an Industry Event in 1989
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.
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At an Industry Event in 1985
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
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.