why my winona ryder phase is forever

Veronica Sawyer's outsider style has informed writer Maya Singer's own since she first identified as "alternative."

by Maya Singer
15 December 2015, 3:15pm

"Sink. Now." My mom shoves my head into the bathroom sink and turns on the tap. I keep my eyes shut, mostly, but when they blink open I see brackish water circling the drain. Mom rinses and re-rinses and rinses again, until the water runs clear.

I am thirteen years old, and my latest attempt to transform into Winona Ryder has ended in yet another abject failure. Don't ask me how I managed to get my hands on a box of black Clairol dye—I don't remember. What I do recall, as though it were yesterday, is the look on my mom's face when she returned from a long weekend away to find her dishwater blond daughter with a pile of gunky brown curls atop her head. Mom was right to insist I wash out the dye—goth didn't suit me. Three boiling hot rinses and two shampoos later, I was back to my boring old self again, just in time for the start of eighth grade at Longwood, Florida's boring old Milwee Middle School. If only washing away my Winona obsession were so easy.

Heathers did it for me. The movie came out in the spring of 89, around the same time I'd started dabbling in college radio and reading Sassy and thinking of myself, in a general way, as "alternative." That term wasn't yet in the vernacular, however—there was no word back then to describe a category of white, honor roll, suburban otherness, and so in the absence of a way of a categorizing myself, I fastened on Winona Ryder as a kind of spirit animal. Which meant, in practice, that I aped her style.

She wasn't my first style icon. First, there was Debbie Harry: I was a kindergartner when I encountered her, guest-starring on The Muppet Show, and though I can't say she influenced my taste, which in those days ran to skirts that spun out when I twirled, I can point to seeing Harry perform "Call Me" in a beaded purple sweat suit as my earliest revelation of "cool." A few years later, Madonna stirred similar awe, and after that, in a twist, I went through an extended Anne of Green Gables phase. And then there was Winona, my true love, the muse I'd always wanted. And the exactly wrong one for me to have.

I look nothing like Winona Ryder. I'm on the tallish side—5'8—and I got there early, reaching full height by high school. My curves filled out around the same time. I've got a stern jawline and swimmer's shoulders, and my thick, irascible hair was, for much of my life, streaked yellow by sun and chlorine. At my thinnest I come off rather lanky, and people tell me I'm a dead ringer for the actress Lake Bell. If, at thirteen, I'd been choosing my muses wisely, I'd have picked Cindy Crawford, likewise sun-kissed and cheek-boned and maned. Or Susan Sontag, a character I didn't encounter until later, to whom I bear a passing resemblance both physically and temperamentally. I could have worn turtlenecks and shot people withering glances over a copy of Camus, and that look would have worked for me. Even in middle school. Instead, I yearned to be Winona, black-tressed alterna-gamine, eyes dark pools in a heart-shaped sea of porcelain skin.

Why Winona? I don't think it was her beauty that appealed to me so much as her way of not entirely possessing it. That mussed bob, those ersatz vintage clothes, the clunky Docs—these seemed to token a person who considered her reflection a foreign thing, one that bore at best a distant relationship to her intelligent interior being. At twelve, thirteen, fourteen—those hard developing years—that attitude felt familiar.

I didn't know what to do with my looks, either. They were a daily event that just happened to me. Winona's haphazard approach to getting dressed struck me as the correct means of expressing a sense of alienation from one's own object-ness. I was allergic to the idea that my physical self—that mask of flesh, imposed by genetic fiat—was the thing people took to be "me." Screw you, I told that physical self. I'm me.

Of course, that "screw you" attitude is the essence of cool. Debbie Harry had it. Madonna, too. Even Anne Shirley, she of Green Gables, was "screw you" cool in her own accidental, puckish way. So there's a through-line. Winona, roughly my peer but old enough to be looked up to, made awkwardness itself seem cool. Even in Heathers—still one of my top-five-favorite films—where she looked amazing, especially in that convenience store scene where she's got on the off-the-shoulder sweater and low-cut pinafore—you had the impression that playing a hot girl was kind of a drag for her. "Drag" as in "putting on drag," i.e., pretending to be that which you are not, and also "drag" in the sense of, what a bore. That was exactly how I felt about my efforts to fit in with my popular-girl friends at school. On both counts.

I embraced Winona because she went against the grain. Her style was subversive. Until it was not. As a kid, aping Winona's grungy, everything-oversize look was a mistake, on an aesthetic level, but it did get the point across. When I moved to New York in my early twenties, however, that slack Winona style was distressingly typical. Indeed, it still is. If I were choosing my muses wisely now, I'd look to someone like Red Desert-era Monica Vitti, properly angsty but nevertheless grown-up polished and in tune with her own sex appeal. Or, I don't know, maybe Sontag again.

Yet I've never been able to shake my Winona thing. Winona herself has evolved—she's very precise and glossy when she turns up in public—but a certain dishabille is baked in, with me. I think, for instance, of a friend's black tie wedding not long ago: I wore a dress of figure-hugging emerald velvet, and red lips, and heels, and people at the reception were all like, "Oh my god, Maya, you look amaaazing...." But I couldn't escape the feeling I'd had—more of a reflex, really—as I studied myself in the hotel mirror before leaving. What a drag. What a pretense. What a bore. When I wear that dress now I wear it with clunky oxfords and a mannish overcoat. Winona forever, I guess. 

We'll be rolling out stories by our favorite writers on their personal style icons all week. Read them all hereWho's yours? 


Text Maya Singer
Photography Max B. Miller/Archive Photos/Getty Images

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