Penelope Tree wears a Miu Miu cape; Lanvin dress; Lisa Eisner Jewelry earrings; Noonday Collection necklace.

Photographed by Tim Walker; Styled by Sara Moonves.

It’s been said of the photographer Richard Avedon that his great genius as a portraitist was his ability to make famous faces funny and funny faces famous—and during a seminal period of the ’60s, when freewheeling flower power was colliding with Kennedy-era chic, there was no funny face more famous than Penelope Tree’s. Arresting in her beauty and unapologetically unique, with enormous eyes, barely there brows, and a kooky, revealing style that got her heckled on the street, Tree—a few days shy of her 17th birthday when she was discovered at Truman Capote’s legendary Black and White Ball—became the ultimate photographer’s muse. A particular pet of Diana Vreeland’s, she beguiled not just Avedon but also David Bailey, who, after turning his lens on her otherworldly visage, fell madly in love with her.

Half a century later, Tree’s ability to inspire hasn’t waned. In fact, in the mind of Tim Walker, who shot the images of Tree seen here, her appeal has only intensified with time. “She is the blueprint of individuality and extreme beauty,” says Walker, who, while working as Avedon’s “fourth assistant” in the ’90s, remembers printing—and marveling over—his boss’s iconic black and white shots of the proto-supermodel in all her waifish glory. “She was Karen Elson before Karen Elson. She trailblazed this idea of difference. To Kate Moss she’s like a goddess.”

Vintage Pierre Cardin dress from William Vintage; vintage Pierre Cardin necklace from New York Vintage, New York. Beauty note: La Prairie Skin Caviar Eye Lift.

Photographed by Tim Walker; Styled by Sara Moonves.

Valentino dress; Manuel Albarran mask; her own bracelet.

Photographed by Tim Walker; Styled by Sara Moonves.

Born in England to Ronald Tree, a conservative politician and heir to the Marshall Field’s fortune, and Marietta Peabody FitzGerald, a Yankee blue blood who later went on to become a U.S. representative to the United Nations Commission on Human Rights, Tree had a childhood that was equal parts privilege and, as she puts it on the phone from her home in England, “benign neglect.” When Marietta grew tired of the U.K., Ronald agreed to move the family to New York, and then quickly decamped to Barbados, where Tree would see him only during the holidays. (He built the storied Sandy Lane resort and would later reveal that he was gay.) Marietta had a series of affairs, most publicly with the 1952 and 1956 presidential candidate Adlai Stevenson. Penelope, largely forgotten, was left to navigate New York City with her friends. In her early teens, when her parents got wind of her wild social life, she was shipped off to boarding school. She was miserable and developed anorexia and then bulimia, from which she suffered until her early thirties.

But, Tree says now, there were upsides to her lack of hands-on parenting: “I was lucky in some ways because I had a lot of freedom, which nowadays kids aren’t given. And because of the way I was brought up, I learned to talk to people in a certain way and not be afraid of meeting people like Cecil Beaton.”

Carolina Herrera dress.

Photographed by Tim Walker; Styled by Sara Moonves.

One fateful meeting occurred in 1966, at the Plaza hotel in New York, with Tree done up for Capote’s history-making fete in trailing strips of black silk over nothing but a pair of scandalously sheer tights. Vreeland, then the editor in chief of Vogue, called her the next day and soon Tree was posing for every big name of the moment. A year and a half later, she and Bailey had fallen in love, and Tree, 18 to his 30, followed him back to England. Perhaps predictably, it was not a happily-ever-after situation. Tree developed a skin condition, which left scars that ended her modeling career, and Bailey wasn’t exactly monogamous. “I appeared sophisticated, but I really wasn’t,” says Tree of that time. “Emotionally, I was probably even younger than my age.” As the relationship collapsed, so did Tree. She was arrested for cocaine possession in 1972 and, after breaking things off with Bailey, moved to Sydney a couple of years later.

Saint Laurent by Anthony Vaccarello blazer and pants; Stuart Weitzman shoes.

Photographed by Tim Walker; Styled by Sara Moonves.

Given all the tumult, it’s not surprising that Tree had very little interest in stepping back into the spotlight for decades. She pulled herself together, raised her children—Paloma Fataar, 39, and Michael MacFarlane, 30—and found peace in the study of Buddhism. Through one of her spiritual teachers she became deeply involved with Lotus Outreach, a charity that provides education to Indian and Cambodian girls at risk of falling victim to sex trafficking.

Celine by Hedi Slimane cape dress; Joelle Kharrat earrings.

Photographed by Tim Walker; Styled by Sara Moonves.

Celine by Hedi Slimane cape dress; Robert Lee Morris neckpiece and necklace (worn as head ornaments).

Photographed by Tim Walker; Styled by Sara Moonves.

But despite the way her modeling career ended, Tree says that she wouldn’t trade those years in front of the camera for anything. “It is very tough at that age to have so much attention on your appearance,” she says. “It’s better instead to develop in all kinds of ways, and I think modeling possibly stops that development, or is not particularly helpful to the emerging personality. But none of it do I regret for a second. All the traveling, and the extraordinary people I met along the way…I’m so glad that I had the experience—even if there were a lot of stumbling blocks and it took a long time to work out.” And while her current life in the English countryside rarely calls for couture—she says she lives in jeans—her fascination with fashion has never wavered. “I’ve loved clothes as far back as I can remember, and I still do,” she says. “I liked my mother’s clothes, and it was the one area where we got along.” In recent years, she’s even done a bit of modeling, appearing in campaigns for Burberry, in 2006, and Barneys New York, six years later.

Still, it was with no small amount of trepidation that Tree agreed to pose for Walker, especially, she says, when she realized—only once she’d arrived on set—that the images they were creating were an homage to iconic shots she did half a century ago with Avedon and Bailey. “Tim didn’t really tell me what he was planning; I just thought I was going to do some fashion shots,” she says. “I had no idea until I saw these pictures on the wall of me 52 years ago, or whatever, and I wanted to run immediately! There is nothing more scary than thinking that you’re in competition with your 18-year-old self. And I haven’t had any reconstruction!”

Saint Laurent by Anthony Vaccarello blazer and pants; Stuart Weitzman shoes.

Photographed by Tim Walker; Styled by Sara Moonves. Hair by Malcolm Edwards at LGA Management; Makeup by Sam Bryant at Bryant Artists; Manicure by Loui-Marie Ebanks at JAQ Management. Produced by Jeff Delich at Padbury Production; Production Manager: Lauren Sakioka at Padbury Production; Photography Assistants: Sarah Lloyd, Tony Ivanov; Lighting director: David Gilbey; Retouching: Graeme Bulcraig at Touch Digital; Fashion Assistants: Allia Alliata di Montereale, Philip Smith, Sandra Blazinskaite, Harry Bradbury, Audrey Johnson; Production Assistants: Charlotte Norman, Harry Hose; Hair Assistants: Lewis Stanford, Vincenzo Della Vope, Thomas Temperley, Nicole Iroh; Makeup Assistant: Claudia Savage; Tailor: Alina Gencaite.

Happily for everyone involved, she was too polite to flee—“Everyone was there bushy-tailed and waiting to go, and I thought, Oh god, I don’t think I can get out of this,” Tree says with a laugh—and the results, of course, speak for themselves. “The fashion industry is perpetually interested in youth, and that’s a mistake,” says Walker, who persuaded Tree to work with him at David Bailey’s 80th birthday party last year. “Penelope is so major and amazing and still so beautiful. These photos are a big up to the beauty of age.”