A New Book Reveals What It’s Like to Be Winona Ryder’s Best Friend

During the late 1990s and early 2000s, an unexpected hideaway for big-name celebrities existed beneath the Marc Jacobs store in New York City. Inside the original flagship on Mercer Street, past the dressing rooms and racks of clothing, into the back of the shop and down the stairs to the basement, the vice president of public relations for Marc Jacobs’ store at the time, Robert Rich, had a windowless office that doubled as a safe space for his famous friends—Winona Ryder, Sofia Coppola, Kate Moss, and Grace Jones among them.

“It was kind of like my clubhouse,” Rich tells me on a recent afternoon from his home in Manhattan. “Nobody could see us. It might be pandemonium outside with paparazzi in the street, but we would all be alright downstairs in the office.” In that basement, Rich spent countless hours photographing the stars that would come in and out of his workspace for fittings (or simply to hang out) with a Polaroid camera. And there, he cultivated what he describes as an “instant trust” and decades-long friendship with Ryder specifically, with whom he became quite close over the years. Standing in front of the infamous “mood board” wall of Rich’s office—where he would tape up pictures he’d ripped out of magazines for inspiration—Ryder felt free to pose with silly abandon, wearing wacky get-ups or making funny faces for the camera.

Now, a collection of those intimate photographs of Ryder will be published in a hardcover book, titled Winona, from the publisher IDEA. The book contains over 100 images of Ryder in Rich’s basement office—but also includes paparazzi photographs of the duo shopping in SoHo or grabbing lunch, straight from the pages of Star magazine and The New York Post. (Rich is described in these articles as a “mystery man.”) There are images from their more glam nights out, like when Rich and Ryder attended the 2009 Met Gala together. “Marc was hosting with Kate Moss, Selma Blair was there, Anne Hathaway was there, Madonna was with Marc because she’d just done the LV ads,” Rich recalls. “And Marc’s table was full of Brazilians.”

And of course, there are a multitude of images from their time spent together as BFFs. “We went to the movies together, we had sleepovers,” Rich says, pointing to photos of Ryder he shot on his bathroom floor. “I was in L.A. a lot and she was in New York a lot, so when I was out there I would see her, and vice versa. And it was so funny, because every time I’d see her, she’d be doing a different movie and I never could recognize her immediately. She was always completely different—with blonde hair, long hair, short hair. It would take me five seconds to realize—oh my god, it’s Winona.”

The two worked hand-in-hand on the book. “I let her take out whatever she wanted or whatever she didn’t like,” Rich says. But when he came to the decision that he’d publish the 20-or-so-years’ worth of photographs in a tome, there were a few pictures he knew he had to include. “The day that we hung out with Kate Moss in my office with Patricia Taylor, Keanu Reeves’s mother—she’s a good friend of mine,” he says. “It was just a fun day. Even Marc stopped by to say hi. Kate was cutting dresses up on Winona’s body; we had long dresses, she’d make ‘em into mini dresses.” Rich believes that was the first time Ryder and Moss met: “I think they saw each other once at a party or something, but it was the first time they talked and hung out,” he recalls. “I always thought they could be friends. It was a great place for them to meet with no one around. And they hit it off.”

But the pictures of Ryder at her most vulnerable do not feature her face at all. There are a group of images that feature her bare midsection, her breasts covered by her hands. They look like they were shot on a flip phone camera, exuding a level of intimacy you just won’t see in professional or editorial shots. Here, though, Rich’s memory gets a bit foggy: “I don’t think there’s a story behind those pictures,” he says. “Maybe we were getting ready because she did the ‘Protect the Skin You’re In’ t-shirt? Maybe we were prepping for that... Because she never took her clothes off before for a photographer. But she did it for Marc—and Robert Rich!”