It tracks that Winona Ryder, every goth girl’s ’90s style icon, would be born just two days before Halloween. From Heathers to Edward Scissorhands, Bram Stoker’s Dracula to The Age of Innocence, the off-kilter and other-worldly characters she’s played on screen seem totally in tune with her off-duty penchant for black slip dresses, white lace, and a bright red lip.
But before she became the poster girl for her era (earning two Oscar nominations in the process), Ryder was a child star who started acting lessons at 12 and made her screen debut at 14, in the high-school drama Lucas, opposite a young Corey Haim and Charlie Sheen. Two years later, Tim Burton came calling with Beetlejuice and the part of the hollow-eyed, shimmying Lydia Deetz, which swiftly made the actor a household name.
Almost a decade ago now, Ryder came back to claim her goth girl crown with a role in the epic Stranger Things. At premieres and fan events season after season, Ryder has kept to her own glamorous, gothic aesthetic: For the Stranger Things 5 premiere in LA, she wore a striking Yohji Yamamoto spring summer 1998 set—Lydia Deetz all grown up.
This week saw Stranger Things finally bid its gang a moving farewell. As Joyce Byers, Ryder embraced the role of a fiercely protective mother, the emotional backbone of the series, who had her rightful full-circle moment in the finale. And so, we present 30 glorious throwback photos from the first decade of Winona Ryder’s career, charting her rise from fresh face to Hollywood heavyweight.
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Two years after her screen debut, a 16-year-old, still relatively unknown Winona Ryder attends the Golden Globes in a neat blazer, skirt, and delicate jewelry. Accompanying her is her then-boyfriend and co-star on 1987’s Square Dance, Rob Lowe, 23, who was nominated that year for best supporting actor. Two months later, Beetlejuice would launch Ryder into the stratosphere.
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Goofing around during a shoot in LA aged 17, now with Heathers under her belt, too.
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Fresh-faced, in a black blazer and floaty white dress, for the 4th Independent Spirit Awards.
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The same blazer now paired with a black minidress and red lip for a Los Angeles benefit.
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A leather jacket and black T-shirt for the opening of a Damian Elwes exhibition in LA.
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In all-black, with a rumpled bob, for the Los Angeles premiere of Michael Keaton’s Batman.
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In a white minidress for the New York premiere of Great Balls of Fire!
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The classically Winonian combo of a black dress and red lip for the LA premiere of Mermaids, in which she co-starred with Cher and Bob Hoskins.
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In a black velvet blazer and minidress for the American Cinematheque Awards’s salute to Martin Scorsese, her director on The Age of Innocence, in Los Angeles.
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Looking remarkably assured in an early headshot.
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In her off-duty uniform of straight-legged denim, band T-shirt, and leather blazer for the LA premiere of The Commitments.
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Twenty years old and shooting The House of the Spirits, in which she appeared opposite Meryl Streep, Glenn Close, Antonio Banderas, Jeremy Irons, and Vanessa Redgrave.
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With her friend and co-star on Bram Stoker’s Dracula and The Age of Innocence, Richard E. Grant, for the New York premiere of his new film, The Player.
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An early instance of method dressing from a 21-year-old Ryder for the LA premiere of Bram Stoker’s Dracula, in which she was directed by Francis Ford Coppola.
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With her new gamine crop and in a purple velvet slip dress for the New York premiere of The Age of Innocence, with her then-boyfriend, Soul Asylum frontman Dave Pirner.
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Back at the Golden Globes in a simple black maxi dress and string of pearls, aged 22—the year she won the best-supporting-actress statuette for The Age of Innocence.
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Dazzling in sequin fringe at the Oscars, where she was again nominated for her supporting turn in The Age of Innocence, but this time lost out to The Piano’s Anna Paquin.
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Now 24 and with a 16-year-old Claire Danes—the Beth to her Jo March in 1994’s Little Women—at the Warner Brothers Studios’s Fire and Ice Ball in LA.
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Delicate finger waves, jewels, and a sparkly ball gown make for a supremely glamorous Oscars look the year Ryder served as a presenter, introducing one of the performances nominated for best original song.
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Attending the LA premiere of Steve Martin’s Sgt Bilko in a ladylike ensemble, with Richard E. Grant in tow.
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With the late, great Giorgio Armani, at an Armani store opening in New York.
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Reunited with Danes at the LA premiere of the latter’s latest film, To Gillian on Her 37th Birthday.
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At 25, pretty in pink at the American Film Institute’s Lifetime Achievement Award salute to Martin Scorsese in LA.
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Leaning into old-school opulence once again, for the American Movie Classics Film Preservation Festival in LA.
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A 26-year-old Ryder with Gloria Steinem at the after-party for The Vagina Monologues in New York.
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In a bold red lip and floor-skimming, sequin showstopper for the Film Society of Lincoln Center’s event honoring Martin Scorsese.
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Chic but low-key at Cannes, the year she served on the jury alongside Sigourney Weaver and jury president Martin Scorsese.
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Going full goth for the opening night of the New York Film Festival.
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Ryder, at 27, in an LBD for the LA premiere party of Eyes Wide Shut.
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A 28-year-old Ryder at the Golden Globes, where she acted as a presenter, alongside her then boyfriend Matt Damon, 29, who was nominated for best actor in a motion picture: drama for The Talented Mr. Ripley.
