There's a Reason You Always Want to Dress Up As Winona Ryder Characters for Halloween
There’s a scene in Reality Bites when Winona Ryder’s character, Lelaina, walks into the living room on her way to the premiere of her documentary series. Ben Stiller (playing Michael, the clueless yuppie she’s dating who romanticizes her idealism) and Ethan Hawke’s Troy (her slacker best friend with whom she’s secretly in love) begin to assess her, and where Michael is so enchanted he has trouble speaking, Troy doesn’t hesitate: “You look like a doily.” (A neg that would launch one million teen crushes, because it was 1994 and that’s how things were.)
Lelaina’s cream-colored, crochet, midi-length dress is a far cry from the slacks, button-ups, and floral dresses that define her wardrobe for the rest of the film. It’s her attempt to grow up and into Michael’s corporate world, and out of the in-between post-graduate life she and her close friends occupy. Insufferable as Troy is, 25 years later few of us celebrate that cream-colored dress when citing the magnificence of Winona Ryder’s style. Because even though we know the entirety of what she wears in Reality Bites is costume, that dress is the only piece that makes it seem like Winona is somebody else.
Hands up if you too worship at the altar of Winona Ryder, or if your autumnal mood boards are covered in photos from her various nineties incarnations; as if she lived and dressed entirely for earth tones and dark neutrals, like a perpetual October queen. All of this would be for good reason. Over the course of the late eighties and nineties, Winona Ryder cemented herself not just as a stylish young actor with access to leather jackets and oversized sweaters. Instead, she came to epitomize the style journey of anyone who feels more comfortable resting outside of mainstream trends. Because even when Winona has been “trendy,” it’s never seemed as part of an attempt to exist on-trend. It seemed like she was wearing whatever she wanted. And then everyone else wanted to wear it, too.
That’s not to say it is rare for celebrities to influence popular fashion, but when we’re seeing someone’s real-life style ethos seemingly reflected in the roles they choose, that’s something else. In films like Dracula, Girl, Interrupted, and Heathers, Ryder's costumes consistently appear to be an extension of who she is as an actual person. Case in point: Three decades after its release, Heathers (a tale about an outcast named Veronica — played by Ryder — who takes on her school’s creme de la creme) remains so beloved that it’s been manifested as fashion and cinematic canon online.
At Heathers’ beginning, Veronica’s style mimics the tailored, ultra-preppy wardrobes (see: blazers) of the clique she’s friends with. But by the end, following murder and mayhem, she’s smoking in a leather jacket, sauntering down the hallway as if to further reiterate how much like her old friends she’s not. Around the same time, in her real life, Ryder was spotted in what’s now morphed into an iconic leather jacket, faded jeans, and graphic T-shirt. Which, at the end of the eighties/start of the nineties made a statement: Ryder wasn’t a Hollywood Heather. And that means the world if you’re not a Heather, too.
Using wardrobe to forge a bond with her audience has been a theme in so many of Ryder’s most beloved roles and the costumes they’ve etched into our memories: Reality Bites sees Lelaina in a thrifted aesthetic (like her short-sleeved gas-station attendant's top); in this role Ryder’s style is looser and a little less rock ‘n roll than the Heathers era. She also looks — and dresses — more grownup. So while her choices still give away how lost and directionless she feels sometimes (the doily dress) they also simultaneously represent the way many of us tend to drape ourselves in pieces that are oversized or muted or easy to wear as a means to feel comfortable somewhere in life. Lelaina always looked awesome, but her clothes weren’t worn as a way for her to stand out.
And that was similar to real-life Ryder the same year: upon winning her Golden Globe in 1994, she showed to the ceremony in a simple black dress and a small string of pearls. She wore, it would seem, something she liked; something she felt comfortable in (she’s always had a penchant for wearing black). And considering the mid-nineties sparked a more formal, fancy approach to awards shows, Winona’s choice attested to the idea that she was happily anchored in what she knew worked. Formalwear can be terrifying. Why wouldn’t you choose something that reflects your tastes instead of something you’d be second-guessing all night?
Granted, to an extent, I’m projecting. But you can’t blame me, especially since Ryder’s characters have so perfectly fallen in-step with autumnal trends we’re still seeing today. As Lydia Deetz in Beetlejuice and Charlotte Flax in Mermaids, Winona donned dark and moody pieces like black blazers, sweaters, and long skirts — plus dark vintage blouses with crisp collars, covered by cozy, pastel cardigans. (Because even at one’s most emo, warmth is key.) Not to mention Autumn In New York: a movie with the season literally in the title, and one in which Ryder’s character, the terminally ill Charlotte Fielding, dons over-size faux fur coats, cream-coloured wraps, and sheer, gauzy dresses contrasted by long, dark jackets with excellent collars. Is it an iconic movie role? Absolutely not. But the wardrobe is an autumnal dream practically made for revisiting right now, as trends of the 2000s continue creeping back into play.
Of course, I don’t know Winona Ryder, nor have I ever been privy to why she’s made her style choices. But I can safely bank on why, for decades, Gen X-ers and millennials continue to look to her various versions of self: Despite how many of us admire this icon, she’s never entirely fit into Hollywood. She’s chosen roles that champion people who live on the outside. She managed to avoid being defined by her long-ago relationship with Johnny Depp (despite him having her name still partially tattooed on his arm) and stepped into roles that were more grownup, complicated, beloved (Little Women forever), and which tackled the complexities of being a person (Girl, Interrupted). And that, together with what she wore (jeans, T-shirts, leather jackets, velvet, black, black, black) created a mythos around Ryder: She isn’t like Them. She isn’t spoken about in the same breath as one director. She is an alternative to the actors (and people) who fit cozily into particular boxes. She doesn’t seem to compromise. She’s just trying her best.
And when thinking about an industry (or society) that puts such an emphasis on authenticity despite so often lacking it, Winona Ryder’s self-awareness is a breath of fresh air. But so are her moments of raw humanity — her complete lack of self-awareness. When she was charged with shoplifting, “Free Winona” became a cultural touchstone, particularly since she was being held so closely under the microscope over a crime that was more puzzling than it was harmful. Equally confusing were her facial expressions onstage during the Stranger Things win at the SAG Awards back in 2017. Or her revelation with Keanu Reeves last year that they might have gotten married accidentally while filming Dracula. (A dream I will carry with me until I die.)
Winona Ryder is as beautifully complex a character offscreen as she is on. So who wouldn’t want to dye their hair black as a means of channeling her, albeit temporarily? Who wouldn’t want to evoke the power of Veronica when confronting a Heather? Who hasn’t struggled to figure out one’s life in the way Lelaina tried to? (Or that Lydia Deetz, in Beetlejuice, tried to; or the way Charlotte in Mermaids did when Ryder was 19.) And wrap themselves in cozy fall layers while they do? Winona Ryder deserves all the places on our autumnal mood boards that we give her. But on top of that, she also deserves recognition for the way her sense of style has united anyone who wishes it were autumn all year long — even those of us who wish we could pull off a doily look with half as much panache.