1Beetlejuice
Getty Images Spiky bangs, punky makeup, and an attitude to match—Winona Ryder became the queen of cool following her role in 1988's Beetlejuice.
2Heathers
Getty Images Feathered bangs and a bouncy blowout at the beginning of the cult-favorite film Heathers.
3Fresh-Faced
Getty Images Ryder wearing the blunt bob that every supermodel is copying in 2017.
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4'90s Grunge
Getty Images Boyish brows and a swipe of metallic lipstick in 1989.
5#CoupleGoals
Getty Images Ryder's red lipstick and her new boyfriend Johnny Depp set hearts (and Tumblr pages) on fire in 1990.
6Slicked-Back
Getty Images The couple that slicks their hair back together, stays together. Well, maybe not—but they look damn good.
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7Edward Scissorhands
Getty Images Depp and a blonde Ryder in the 1990 film Edward Scissorhands.
8Black-and-Red
Getty Images Jet-black and flippy hair was en vogue in 1991. We love how she paired it with skinny brows and a deep red lipstick.
9Classic Beauty
Getty Images Ryder's natural curls were on full display in 1992.
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10The Short Cut
Getty Images Ryder takes a cue from Mia Farrow and owns the short, layered pixie cut.
11'90s Beauty
Getty Images Ryder and Claire Danes are the epitome of '90s beauty (matte skin, frosty lipstick, skinny brows, side-parted pin) in 1996.
12So Frosty
Getty Images The only thing frostier than Ryder's lipstick is her newly-styled pixie cut.
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13Back to Red
Getty Images Red lipstick is one of Ryder's signature looks, in 1998 and now.
14Spiked Up
Getty Images A short and spiky haircut calls for a little more makeup than Ryder usually wears—black eyeliner, gray eyeshadow, frosty berry lipstick, and ultra-plucked '90s brows.
15The Headband
Getty Images Only Ryder could make a courtroom appearance look this chic—thanks to a black headband.
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16Easy Updo
Getty Images Ryder's signature smudgy eyes look fresh paired with bronzed skin and an easy updo.
17New Grunge
Getty Images The Stranger Things star went back to her roots with a curly, rock and roll hairstyle flipped to one side. Paired with tons of black eyeliner, Ryder proves that punky beauty never goes out of style.
18Soft Curls
Getty Images Ryder accepts the Screen Actors Guild Award wearing face-framing ringlet-tendrils.
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19Winona Forever
Getty Images It's 2017—and Ryder is still at the top of her game with the new hit season of Stranger Things. Just like her preference for deep crimson lipstick, some things never change.
Jenna Rosenstein is the Beauty Director at BAZAAR.com. While attending NYU, she held internships at Women’s Wear Daily, Bloomingdale’s, Harper’s BAZAAR (as Glenda’s intern!) and Allure, the latter of which she parlayed into her first job as the Beauty Assistant. She left Allure three years later as the Senior Beauty Editor, spent a few months at Refinery29 in the same title overseeing branded content, before finally landing back at BAZAAR to oversee all digital beauty content. When she's not testing every lipstick known to mankind, getting zapped by new lasers, or interviewing experts and celebrities, you can find Rosenstein re-watching Star Wars movies, reading books about new discoveries in science and health, and playing with her Bombay cat named Maddie.
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