At sixteen, four days before her seventeenth birthday, a girl walked into Truman Capote’s legendary Black and White Ball wearing a homemade black-and-white outfit so unlike anything else in the room that it stunned everyone who saw her. Her name was Penelope Tree. Tall, wide-eyed, and unconventional by the standards of the era, she was described by one observer as looking like she had arrived from somewhere else entirely. By the next morning, the editor of Vogue had personally called her, and two of the most powerful photographers of the time had agreed to make her a star.
In a single night, she went from an unknown teenager to the most talked-about face in fashion—a spark for a cultural moment that would ultimately cost her nearly everything it gave her. Penelope Tree was born on December 2, 1949, in New York City, into a family that was anything but ordinary. Her mother, Marietta Peabody Tree, was a socialite and political activist so well connected that she represented the United States on the United Nations Commission on Human Rights, moving among presidents and ambassadors as if it were routine. Her father, Ronald Tree, was a British-American investor, journalist, and Conservative member of Parliament who, in his spare time, reportedly helped invent something—because why not add that to the family résumé.
Penelope also had an older half-brother, Jeremy Tree, who became a respected racehorse trainer, and an older half-sister, Frances FitzGerald, who won both a Pulitzer Prize and a National Book Award for her journalism covering the Vietnam War. She was also the niece of Endicott Peabody, then governor of Massachusetts. Growing up, she was surrounded by diplomats, politicians, and war correspondents rather than ordinary neighbors—which meant that when things went wrong for her, and they went very wrong, there was no shortage of people around who cared deeply about appearances and very little about what lay beneath them. That obsession with appearances began early and forcefully.
In 1962, when Penelope was just thirteen, photographer Diane Arbus—who would later become one of the most important American photographers of the century—shot her for Town & Country magazine, a publication usually filled with the soft, flattering social portraits that families like the Trees expected and paid handsomely for. Arbus was not known for soft, flattering pictures of young girls, and in Penelope’s unconventional thirteen-year-old face, with its large eyes and unusual features, she found exactly what she was looking for. Penelope’s father was not pleased. According to multiple accounts of her life, he actually threatened to sue if the photos were published at all.
Not because they were cruel, and not because they exploited her, but because, in his view, they made her look unattractive—and unattractiveness was apparently a legal matter in that household, one worth involving real lawyers rather than, say, having a conversation with his daughter about how she felt seeing herself portrayed that way. For a few years after that, little happened, at least on paper. Penelope grew up moving between family homes in Manhattan and the English countryside, developing what those around her described as an eccentric, sometimes provocative personal style—the kind of look that occasionally got her mocked by strangers on the streets of New York, a harsh way to spend your teenage years, being publicly ridiculed for a face you didn’t choose and couldn’t change. She was, by no means, the type of personality the fashion industry was chasing.
She was just a teenager whose father had openly rejected her appearance, with lawyers involved. Then, on one night in November 1966, everything turned upside down, completely and instantly. Truman Capote, riding high on the success of In Cold Blood and at the peak of his fame, decided to throw the party of the decade. Officially, the Black and White Ball, held on November 28, 1966, in the Grand Ballroom of the Plaza Hotel, was in honor of Washington Post publisher Katharine Graham, but it was really about Capote proving he could summon anyone he wanted.
He invited 540 guests, and the New York Times, in an unprecedented move, published the full guest list the next day. The guest list included Frank Sinatra and his then-wife Mia Farrow, Andy Warhol, Norman Mailer, Henry Fonda, economist John Kenneth Galbraith, and nineteen-year-old Candice Bergen, who wore a mask designed by Halston and described the scene as “New York at its most ferocious. ”
Into this overwhelming crush of egos, money, and masks walked sixteen-year-old Penelope Tree, four days shy of her seventeenth birthday, wearing an outfit she had designed herself with the help of a then-unknown designer named Betsey Johnson—years before Johnson became a fashion landmark. A black V-neck tunic, divided into long hanging panels, over sheer black tights.
No elaborate mask like the rest of the room. No borrowed jewels suggesting old money. Just a teenager in a handmade outfit that looked like nothing else in that glittering room. It should have been a disaster.
But instead, it made her a legend overnight. Diana Vreeland, editor-in-chief of Vogue and without question the most powerful figure in American fashion at the time, called Penelope the next morning. Word also reached Cecil Beaton and Richard Avedon, two of the biggest photographers of the era, who reportedly agreed to work together specifically to make her a star—a minor miracle in a world of competing egos. Within days, the same girl whose father had once threatened a lawsuit over her face was being fought over by the most powerful figures in fashion, all suddenly certain that this particular face would define the coming years of culture.
The same face her family had considered a flaw just four years earlier. Nothing about her had actually changed in those twenty-four hours. The only thing that changed was people’s willingness to look at her and call her beautiful instead of strange. The following year, when John Lennon was asked to describe Penelope Tree, he reportedly summed her up in six words: “exciting, exciting, exciting.
intelligent, intelligent, intelligent. ” That quote would follow her for decades. Suddenly she was everywhere—on magazine covers, at parties, treated not as a passing fad but as proof that standards of beauty were changing in real time. What made her genuinely different from Twiggy, the other dominant face of the era, was that Twiggy’s appeal was based on a fragile, childlike simplicity, while Penelope’s whole look was strange, angular, almost alien—exactly the kind of face that would have been considered a flaw rather than an asset a decade earlier.
Fashion editors loved presenting her as evidence that culture was finally embracing something other than traditional beauty. In 1967, Penelope Tree met photographer David Bailey. If you’ve heard anything about the Swinging Sixties, you’ve likely heard of Bailey—an East End boy turned one of Britain’s most influential photographers, the man who practically invented the visual language of the decade. Before Penelope, Bailey had already built a reputation dating some of the most photographed women alive, including model Jean Shrimpton, whom he discovered and helped turn into one of the decade’s first supermodels.
In other words, this was a man with a well-established pattern of falling in love with the women he photographed. He was twenty-nine when he met her. And here’s the part usually glossed over in the dreamy reminiscences of their alleged great love story: Bailey was married. His wife was French actress Catherine Deneuve, whom he had married in 1965 and would not officially divorce until 1972.
In 1967, the year it all began, Deneuve’s twin sister, Françoise Dorléac, died in a horrific car accident. A marriage already collapsing under the weight of a devastating family tragedy, and in the middle of it, a man in his thirties begins a relationship with a seventeen-year-old he met through work. Nobody at the time seemed to think it deserved a second look. By the end of 1967, Penelope had left Sarah Lawrence College and moved directly into Bailey’s flat in London’s Primrose Hill.
She turned eighteen that December, meaning yes, some of the earliest days of this relationship happened while she was still a legal minor in the United States. She moved her entire life across an ocean for a man who was still married and more than a decade older. The two became, according to reports written decades later, the actual center of London’s sixties scene, photographed together everywhere, treated as one glamorous unit rather than two separate people with inner lives nobody bothered to ask about. From the outside, it looked like a stunning transformation—an unknown girl discovered at a party, moved to London, dating one of the most famous photographers alive, appearing in some of the most iconic fashion images of the entire decade, images still hanging in museums today.
From the inside, according to what Penelope herself admitted later, after decades when she finally had the ability to express it, it felt very different. Bailey’s pattern of falling in love with his subjects was already well established by the time she appeared, and it would continue for years after she left his life. He married four women in total over his lifetime, many of them models or actresses he met on shoots. Decades later, his memoirs publicly discussed his relationships with Shrimpton, Deneuve, and Penelope herself, treating them as glamorous chapters in his personal legend rather than as separate women who each had to cope alone with the consequences of dating one of Britain’s most photographed men.
This is where things get truly sad. Penelope stated in interviews decades later that she appeared far more sophisticated than she actually felt, and that emotionally, she was probably younger than her real age. She grew up in a family that didn’t acknowledge feelings—the same family that once threatened a lawsuit over a photograph rather than talking to her as a normal human being. So when things began to go wrong in the relationship, and according to several accounts, David Bailey was not entirely faithful during this period, Penelope had no tools to deal with any of it.
No outlet, no one to talk to, nothing but the manufactured silence she had been raised in. Around 1970 into 1971, Penelope developed a severe case of adult acne, which she has since linked, in her own words, to a combination of stress, hormonal imbalance, and an eating disorder she has publicly discussed struggling with during this period of her life. Her face swelled and scarred—the same face that had made her famous just a few years earlier. By 1971, her modeling career was effectively over.
Not because she had made a mistake, or a bad business decision, or failed at her job in any traditional sense. It ended because the very industry that had built its relationship with her around her face decided that face was no longer good enough, through no fault of her own. She described how she went from the most sought-after face in fashion to a persona the industry avoided talking about, because apparently no one could handle her new look, as if her scarred skin had become a forbidden, embarrassing topic in polite conversation. If the end of her career was the bottom, what followed was somehow worse.
In 1972, with her relationship with Bailey collapsing and her career completely dead, Penelope bought cocaine from a dealer operating out of a derelict flat in London. The dealer was arrested almost immediately, outside, and Penelope was taken in with him, for the unfortunate association and, to be fair, actual possession of cocaine. What happened next is one of the most quietly painful details in this entire story. Scarred, exhausted, her features no longer resembling the face Richard Avedon had once shot for a Vogue cover, Penelope was held overnight in police custody because the officers simply didn’t believe her when she told them who she was.
They didn’t believe she was a famous former model, nor the daughter of extremely wealthy, well-connected parents who could have posted bail in about ten minutes with a single phone call. To the police, she was just another broken, addicted young woman telling a fantasy story about being someone important. She looked too different from the girl on the old magazine covers. She has since described the whole experience in one devastating sentence: she said that, in a way, she had been stripped of her entire identity.
A girl who was given her entire identity overnight by the admiration of strangers in 1966 now sat in a cell in 1972, having that same identity taken away just as quickly, this time by the disbelief of strangers. The mechanism worked in exactly the opposite direction. Between them, six years, almost to the month. Her sense of self was never her own, in either direction.
It depended entirely on whether the people looking at her that day were willing to recognize her. In 1974, after seven years together, Penelope and David Bailey finally ended their relationship. She left London entirely, moving to Sydney, Australia, putting an entire ocean between herself and the glamorous machine that had made her a star and then discarded her once she stopped being useful. No farewell tour, no dramatic exit interview, just a plane ticket and a firm decision.
In Australia, she married South African musician Ricky Fataar, who had toured the world with the Beach Boys and played with a band called The Flames. They had a daughter, Paloma, who later studied at Bard College and became involved in Tibetan Buddhism and music. Penelope later had a second child, a son named Michael Macfarlane, from an Australian Jungian analyst named Stuart Macfarlane. In the midst of all this, Penelope found Buddhism—a practice about honestly confronting your inner life without turning away from it, the complete opposite of everything her upbringing had taught her.
Then, for nearly four decades, Penelope Tree disappeared entirely from public life. This was a choice, not a collapse. She wasn’t forced out of the spotlight by scandal, wasn’t compelled to hide, wasn’t canceled or blacklisted. She simply walked away from it all.
She raised her children, built her spiritual practice, and lived a full life that had nothing to do with cameras or magazine covers or the approval of editors who had once decided her entire worth based on one outfit at one party over fifty years earlier. Then in 2024, at age seventy-four, she finally did something she’d never done before in her eventful life. She wrote a novel. Titled A Piece of My Heart, it follows a teenage character named Ari with unusual features, who drifts into modeling, falls into a difficult relationship with an older photographer, and watches her career collapse after developing adult acne.
Penelope insisted, repeatedly, in every interview she gave promoting the book, that it’s not purely autobiographical, that Ari’s story diverges in directions that don’t exactly match her real one. But the parallels are impossible to miss. In interviews about the book, she strongly pushed back against what she called the “Austin Powers” caricature version of the sixties, insisting that for those who actually lived through it, especially young women with no institutional protection and no vocabulary for consent or self-esteem, the decade was darker under the miniskirts than nostalgia industries like to admit. She was also blunt about how unformed feminism was at the time, noting that girls of her generation basically had no framework for understanding their own value outside of how the men and magazines around them chose to treat them on any given day.
Throughout almost her entire life, Penelope’s identity was imposed on her by other people, over and over, in ways she never actually agreed to. A father who threatened lawsuits over her photograph when she was thirteen, deciding on her behalf that her face was a burden. An editor who called the morning after a party, deciding on her own that she should become famous without ever asking if that was what Penelope really wanted for her life. An industry that dropped her the moment her face changed, through no fault of her own, and never looked back to see how she was actually doing once the cameras stopped.
A partner who was unfaithful and left her with no way to process the trauma. Police officers who refused to believe her account of her own identity, even though her life story was available for verification. Piece by piece, decade by decade, away from the public eye and with no applause at the time, she quietly took her life back, one piece at a time, on her own schedule. She chose a marriage that gave her children, far from the fashion machine.
She chose a spiritual practice that gave her a language for her inner life for the first time. And at seventy-four, after decades of the industry having no reason to care about her news, she finally chose to write her own words on her own pages, on her own terms, rather than letting someone else’s camera define what her story meant to history.