Fans of Winona Ryder lined up outside Dover Street Market in Manhattan on a recent chilly evening to attend a launch party for “Winona,” a book of Polaroids and cellphone shots of the Gen X cultural idol.
“She’s so famously private that any peek into her interior life is delicious,” Daniela Tijerina, a writer and editorial assistant for Vanity Fair, said. “I’ve molded so much about my own style after a woman I know so little about, and that makes her as cool as a person can possibly be.”
The shots in the book were taken by Robert Rich, who started photographing Ms. Ryder soon after becoming friends with her more than 20 years ago. His images capture her in unguarded moments: eating pizza during a sleepover at his Hell’s Kitchen apartment; and smoking a cigarette in a bathroom, while the model Daria Werbowy quoted lines from “Reality Bites” to her.
At the party, Mr. Rich, 57, signed copies of his book, as guests mobbed a merch table selling T-shirts, caps and tote bags, all of which read: “Winona.”
“What we love about Winona is that you know nothing about her,” Mr. Rich said. “We love that she’s a mysterious woman. I used to never recognize her when I’d meet her. She’d always be wearing a visor or a pageboy cap. I’d walk through the city with her, and no one even knew who I was with.”
He befriended Ms. Ryder when he was a manager of the Marc Jacobs store on Mercer Street in SoHo in 1999. The shop was a hangout for Selma Blair, Sofia Coppola, Parker Posey and Kate Moss, and Mr. Rich often took Polaroids of celebrity clients in his basement office.
He got to know Ms. Ryder during fittings at the store and later helped dress her in Marc Jacobs pieces for parties, premieres and magazine photo shoots. After Ms. Ryder’s shoplifting trial in 2002, he became a confidant during a period when she retreated from public view.
A year ago, Mr. Rich found himself thinking about all the Polaroids he had amassed in several shoeboxes in his closet, and he texted Ms. Ryder about the idea of collecting them in a book. After she said yes, the London-based book dealer and publisher, Idea, took on the project. Marc Jacobs wrote the foreword.
As the party guests sipped champagne and flipped through the book, Mr. Jacobs made an appearance.
“She was our young Garbo,” he said. “A Winona sighting was always a big deal back then. She came to one of my shows at the time, and I still remember she was a little like a deer in the headlights. She’s not snobbish. She’s not the red carpet girl. And that has always added to her cachet and cool.”
Francesca Sorrenti, who designed and edited the book, reflected on Ms. Ryder’s enduring appeal.
“To understand Winona, you have to understand the youth movement of the 1990s,” she said. “There are only a few personalities quite like hers out there at any given time, and in her era, it was Kate Moss and Winona. You’d just see them and you’d want to know, Who is that?”
“I’ve hung out with Winona,” Ms. Sorrenti added. “And yes, she’s shy, and that shyness also projected itself into what her fans consider her mystique.”
Hanging out by a rack of Comme des Garçons jackets was Inna Blavatnik, a creative director. “I’m of the Generation X era that Winona represented,” she said. “It was all about having a moody cool and not giving a you-know-what, and she became my role model as a teenager.”
As the night progressed, the fashion designer Zac Posen and the musician Joe Jonas stopped by — and a question loomed: Would Ms. Ryder show?
“I texted her about the party,” Mr. Rich said, “but I haven’t heard anything back yet.”
The filmmaker Zoe Cassavetes offered: “I’ve known Winona for a long time, and when you get to know her, she’s extremely present and generous, but she’s also good at disappearing into the ether.” She concluded: “If she were coming, she wouldn’t tell anyone she was.”
Ms. Ryder ultimately never materialized, but Jayna Maleri, a fashion editorial director, said she preferred it that way. “I almost never want to see Winona Ryder in person,” she said. “Not because I think she’d disappoint me, but because she occupies a place in my brain so rooted in my nostalgia that it would be jarring.”
“She’s an icon of my youth, the eternal cool girl who embodied the authenticity of the ’90s,” she continued. “And I want to hold onto my illusions of her.”
