Celebrity Transformations Winona Ryder's Beauty Evolution From '90s It-Girl to On-Screen Mom Is there any look the actress can't pull off? By Krista Carter Krista Carter Krista Carter is a writer and editor with nearly a decade of experience working in beauty and fashion. InStyle's editorial guidelines Updated on January 9, 2023 @ 09:07AM Trending Videos Close this video player 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 1985 Seth Poppel/Yearbook Library The spiky-haired eighth-grader was mistaken for a boy by her classmates at Petaluma Junior High School in California. 14 Androgynous Haircuts You'll Want to Take Straight to Your Stylist 02 of 24 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 1989 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 1992 Getty Images The Dracula actress highlighted her milky complexion with blood-red lipstick and dark-dyed locks. 05 of 24 1994 Globe Photos Ryder sported the perfect tousled shag in the Gen X opus Reality Bites. I'm Still Not Over Winona Ryder Choosing Ethan Hawke Over Ben Stiller in 'Reality Bites' 06 of 24 1997 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 1998 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 2000 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 2001 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 2004 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 2005 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 2006 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 2008 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. The 23 Best Dry Shampoos for Just Washed-Looking Hair, Tested & Reviewed 14 of 24 2009 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 2010 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 2012 ©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 2013 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. The 30 Best Long Bob Haircuts, According to Celebrity Stylists 18 of 24 2014 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 2015 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 2016 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 2017 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. How to Blend Makeup Flawlessly, According to the Pros 22 of 24 2019 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 2020 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 2022 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. 15 Shag Haircuts for Any Face Shape