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Like the stories surrounding Charles Wintour’s handling of the tragic news of his first child’s death, there are variations to the story of the sudden demise of Anna’s school career. The only thing that’s documented is a simple notation in the records of North London Collegiate School. According to the archivist, Elen Curran, Anna “was here from 1963 to 1966.” Nothing in the records speaks of her graduating. While she is one of the most famous and successful women to have attended North London Collegiate, she left barely a trace of herself. As Curran states, “Sadly, we do not have any further information of Anna Wintour in our archive.”

Anna entered the hallowed halls of North London Collegiate for the last time one day in July 1966, age sixteen, wearing a skirt way above her knees. She was spotted by McLauchlan, who decided to make an example of her.

“Anna was always six months ahead of fashion,” Charles Wintour once said in discussing the end of his daughter’s schooling. “At North London Collegiate she was getting on famously until a new headmistress arrived and spotted Anna’s miniskirt. She stood Anna on a table and ripped her hems down. Then Anna had to go home on the tube in a torn skirt, and quite seriously, it finished her interest in academic life.”

As Drusilla Beyfus Shulman recalls the incident, it not only ended Anna’s “interest” in schooling but caused her actually to quit North London Collegiate a year early. “Anna didn’t graduate from anywhere.” According to her version of the events, “Anna cut her gym skirt so that it was above the knee—I mean
well
above the knee, which was a very prophetic thing to do in terms of fashion. Those
very
short skirts had only just kind of kicked in. Anyway, her French mistress lifted Anna up onto the desk and said, ‘Look at this girl! She’s not worthy of this great school, and she’s just obsessed with clothes. She can go home!’ And so Anna left North London Collegiate and never went back.

“Anna’s rather proud of the story. It is entirely—
entirely
—consistent with her character—
very
self-possessed and also with this sort of sense that she was doing the right thing.”

Whichever way it happened, Anna had permanently finished her formal schooling at sixteen, leaving in a snit over having to play by the rules. Her last day was July 27, 1966.

“She was rebellious and clearly had had it with school,” states Lasky.

Anna’s parents’ worst fear had been that she wouldn’t go to college; they never expected her to be a high school dropout.

“I guess I went the other way,” Anna acknowledged many years later. “My sister always had this joke when she left a message on my answering machine. She asked if I was at the hairdresser’s or the dry cleaner’s. So I was always the bimbo.”

Now the Wintours were concerned about Anna’s future and had come to the realization that her preternatural preoccupation with fashion wasn’t just a phase as they first thought. Her father’s dreams of her following in his footsteps were also dashed because she wasn’t interested in working in the newspaper business, in getting her delicate hands soiled with printer’s ink. As Anna
has stated, she never tried to “prove anything” to her parents. Her interest in fashion was all-consuming, but what she would do with that interest was still undefined and unfocused.

“I’m not a very introspective person,” she once said, reminiscing about that period. “So I didn’t have a great game plan for life.”

I
n the fall of 1967, Anna’s class at North London Collegiate was completing its final semester. Following in Nonie Wintour’s footsteps, Vivienne

Lasky had been accepted at Radcliffe. But Anna had no interest in the traditional markers of young adulthood, like going to college or moving out of the family home. In the Wintours’ downstairs flat she played at being grown up.

Instead of pursuing academics, Anna, with help from her father, was accepted into a training program at Harrods, where she worked in every department with the goal of becoming a buyer. At one point, she was assigned to learn all facets of the jewelry business; at another she sold scarves and accessories in the Knightsbridge emporium’s groovy teen boutique, her favorite department in the store.

Since it was a work-study program, Anna also took courses at a middling Trafalgar Square–area fashion school at the behest of her parents, who thought that even in fashion she should have some sort of formal schooling. Anna almost torched the place during a classroom experiment that apparently had gone awry. The way Anna later recounted the incident to Vivienne Lasky, she mixed and matched a couple of fabrics with some chemicals, put a match to them—and
whoosh
. Anna’s matriculation didn’t last very long; she soon lost interest in what the school had to offer—you either know fashion or you don’t, she protested when she dropped out.

Next to fashion, Anna’s major passion was men—attractive, older achievers.

“She had many boyfriends,” her father once said. “She was once literally chased around the house by Indian statesman Krishna Menon.” Wintour never stated whether he thought the fatal heart attack Krishna Menon suffered at the age of seventy-seven in 1974 was brought on by his supposed hot pursuit of his comely daughter. He also never mentioned he and Krishna Menon had been students at Cambridge together and that the story, which he told to a London newspaper, might have been a fabrication.

“I’d see Anna around and I’d think, ‘What is it these guys see in her?’” Paul Callan remembers. “There was this mystery about Anna, hiding behind her hair, peering out, appearing so shy. Of course nobody knew that behind all that was this fierce girl very much like her father, very Wintourian, purposeful, everything planned, very clever.”

While working at Harrods, Anna met and began dating Peter Gitterman, who was thought to be the stepson of the brilliant conductor Georg Solti, music director of London’s Royal Opera House and later principal director of the London Philharmonic Orchestra, which gave the young man entrée into London society.

“He wasn’t particularly good-looking, but he was interesting and smart,” says Lasky. “He clearly adored Anna and had this mad crush on her.”

For her part, Anna was especially intrigued by Gitterman’s circle of celebrity friends, a rarefied crowd that included Rudolf Nureyev and members of the royal family, such as Princess Margaret’s husband, the fashion photographer Antony Armstrong-Jones, better known as Lord Snowdon. Through Gitterman, Anna met Peter Sellers, Vidal Sassoon, Mary Quant, among others. Anna’s interest, however, posed a dilemma. While she was enthralled with him, she couldn’t have cared less about his great passions—the symphony, opera, and ballet.

In a quandary, she approached Lasky for guidance. “Anna didn’t know anything about any of those things, so she felt rather insecure. I said to her, He really likes you, he’ll probably like teaching you, but you should read up.’ ” Anna took Vivienne’s advice and crammed as if she were preparing for the Oxbridge exams, so as to not embarrass herself. “Because she liked and dated this guy, she learned opera fast, and ballet, too. The next thing I knew, she told me, ‘I’m going to the opera! What shall I wear?’”

Eventually the romance faded, and so did Gitterman, who disappeared from the scene. Around the same time Anna quit the Harrods training program.

For a time she dated a good-looking left-wing figure named Robin Blackburn, who gave lectures at the London School of Economics focusing on the Cuban revolution and wrote for the
New Left Review
. Charles Wintour once described Anna’s preparations to go to an anti–Vietnam War rally with Blackburn. “Having spent two hours wondering what you wore to a demonstration,” her father recounted, “I heard her patter down the steps, turn and run up again. I opened the door and she said, ‘Daddy, am I for or against Cambodia?’”

While Wintour made light of his daughter, and had long ago come to the realization that she wasn’t destined for rocket science, Blackburn says he didn’t think she was as much of an airhead as her father made her out to be.

“I suppose compared with Anna’s later development, or with Charles Win-tour’s own then-politics, he found this bit a cause for remark,” says Blackburn years later. “Her father’s implying Anna didn’t know anything about politics isn’t my memory of the matter.” Blackburn, who went on to become a professor of sociology at the University of Essex, says that besides accompanying him to the demonstration, Anna had made a short visit to the United States and returned with a gift of several books about the war in Vietnam, which he found quite useful, although he acknowledges that Anna may have bought the books based “on someone else’s advice.” But, he adds, “She seemed to have some knowledge of political life.”

After their romance ended, Anna and Blackburn remained friends. In the seventies, he became part of her social circle that included Patrick Wintour and up-and-coming literary darlings like the novelist Martin Amis and the hard-drinking journalist and later American TV talking head and
Vanity Fair
scribe Christopher Hitchens, who early in his career wrote editorials under Charles Wintour at the
Evening Standard
.

A
nna had bought the Vietnam books for Blackburn in New York City during a monthlong stay with her mother’s favorite first cousin, Elizabeth “Neal” Gilkyson Stewart Thorpe—the Stewart and Thorpe signifying her first and second husbands—who was then an articles editor at
Ladies’ Home Journal
, where she handled personality pieces and cover stories, and conducted interviews
with celebrities and politicians, ranging from Carol Burnett to a chief justice of the Supreme Court. She also had worked at
Redbook
as a fiction editor.

Anna, who had dual citizenship because of her mother, had decided on the New York visit, her first such trip on her own, to scope out the possibility of jobs on Seventh Avenue and to look into possibly attending fashion schools. Thorpe hardly knew Anna—a first cousin once removed—and had met her on only a couple of occasions when she was just a child.

Thorpe looked forward to Anna’s visit. With her two sons from her first marriage away at boarding school, she gave Anna one of their bedrooms and settled in for a fun time with hopes of getting to know her better.

She was stunned by Anna’s maturity, sophistication, and style. “My God, I was so impressed by how she dressed, how she carried herself, how pretty she was.” But she also felt that her cousin’s daughter showed little intellectual depth and thought her interest in fashion was shallow. As it turned out, the magazine editor and the future magazine editor didn’t bond.

“We had no connections over the fact of magazines,” she says. “Anna’s interest was solely fashion, and I was totally uninterested in fashion, so we really did not have a lot in common. I was interested in literature, writing, she was interested in clothing. It was fashion that eventually led Anna to magazines,
not
an interest in magazines.”

Thorpe tried her best to entertain Anna, but she was repaid with an unfriendly, cold attitude, and things quickly went downhill.

Anna’s departure left a bad taste in Thorpe’s mouth. Her sister, Patti Gilkyson Agnew, Nonie Wintour’s other favorite first cousin, who lived in New Mexico, says Anna’s lack of gratitude for her stay left Neal feeling hurt and used. “Neal can never forget that Anna never said as much as ‘thank you for letting me live with you for a month and eat dinner with you.’”

The visit underscored the frigid relationship Anna has always had with her mother’s American relatives. Some of that was almost certainly due to the ocean of distance between them. But even after Anna settled permanently in New York, she made no effort to bond with any of them. “She never even got in touch with me,” Thorpe says.

The only other time Anna spent with the American side of her family—an interesting and creative lot—was in the early sixties, just before she enrolled
at North London Collegiate. Nonie, along with her sister, Jean Read, an editor for New American Library, brought Anna, James, Patrick, and Nora to a reunion of the Gilkysons and Bakers at a beautiful wildlife area in central New Hampshire called Squam Lake. There, the Gilkysons had rented a group of summer cottages; besides Nonie and her brood, family members came from New Mexico, California, and Pennsylvania.

Anna met a number of her cousins, two who arrived with their parents from Hollywood, where their father, Hamilton H. “Terry” Gilkyson III, was a well-known musician and composer. One of them, Nancy Gilkyson, Anna’s second cousin, who later had a career as an executive at Warner Bros. Records, recalls, “Nonie and my parents that summer had a wonderful time and laughed all the time. After that summer, I wrote to Anna and she wrote to me for about a year, then we lost touch.”

Gilkyson’s sister, Eliza, about a year younger than Anna, remembers Anna at the reunion as being
“so
beautiful, beautiful and remote. She was not warm, not friendly. That was the only time our paths crossed. I never met or saw her again.” She later became a singer of her own compositions dealing with sex, drug addiction, and death. Eliza and Nancy’s father’s songs were recorded by the likes of Johnny Cash and Tony Bennett. With his group, Terry Gilkyson and the Easy Riders, he cowrote such hits as “Marianne” and “Memories Are Made of This.”

Few, if any, in Anna’s circle ever knew she had such interesting American relatives. She never talked about them and acted as if they didn’t exist. It was as if she was ashamed of, or denied, her mother’s American heritage. Anna considered herself British through and through, at least back then.

V
ivienne Lasky had only just arrived home from her freshman year at Radcliffe, in the summer of 1969, when Anna rang her up. “Oh, you’re back. Good. I have this new boyfriend. We’re fixing up this place. I’m at his parents’ house. You
must
come over this very moment.”

Thinking “typical Anna—
bossy,”
Lasky nevertheless was thunderstruck. New boyfriend? His parents’ house? She’d received many letters during the school year from Anna on everything that was going on in her life but, curiously, not a scintilla of news about a new man. Anna, who enjoyed playing head games with Lasky, was savoring the juiciest for last.

It was warmer than usual that summer in London, and Lasky found Anna ensconced poolside on the beautifully manicured grounds of her boyfriend’s parents’ Georgian revival mansion in the estate area of fashionable Highgate. Lasky was shocked to learn that Anna and Steve Bobroff, a tall, handsome, dark-haired,
veddy
British, trendy and talented freelance fashion photographer about five years her senior, were living together. And Bobroff appeared to be quite a catch—the scion of a wealthy Jewish family who made their money in real estate development and furniture.

“Anna,” says Lasky, “was quite smitten with him. This was a whole new world to her. It was very serious, and it all seemed so natural. There were
many
crushes. This was clearly a different step for her.”

At nineteen, Anna had moved out of her basement flat in the Wintour
home and into Bobroff’s charming carriage house–studio, the first of a number of live-in relationships for her. Their place was located near the historic Vale of Heath—where people fled during London’s cholera epidemic in the late eighteenth century—in Hampstead Village, a hip area of London favored by artists, writers, and the rich and famous.

“Clearly, she thought that with both their talents they could conquer the world,” Lasky believes. “They seemed really close. They thought they had it all. Not that I didn’t think he had talent, but he was all bought and paid for by his parents. He had to prove himself. I had misgivings.”

Anna and Bobroff’s place was a knockout. On the ground level was his starkly modern, all-white photographic studio, furnished with contemporary Italian chairs in primary colors, all top-of-the-line, a kitchen, and changing rooms for models.

Carpeted stairs up led to a minstrel gallery surrounded by leaded-glass bay windows where Anna and Bobroff lived—all taupe and gray, with beautiful flower settings everywhere and a wonderful window seat. “I thought, ‘Wow! Just the most unusual space,’” Lasky recalls. “It was
so
clever what Anna did—sort of a mixture of living room–dining room, with a big oak refectory table, and a bedroom. It was
minute
but exquisite. She was always fussing with the candlesticks—‘Do you think these pewter ones are right for the period, Vivienne? Well, do you?’”

Anna was worried about what her parents would think about how she had decorated the place and what she served them for dinner when they visited. But she wasn’t concerned with what they thought about her living arrangement. “Knowing Nonie and Charles as I knew them,” says Lasky, “they said, let her try, let her fall on her face. The Wintours were never critical of what she did—that was their thing. Why fight it? It would only make it worse. And he was a charming fellow with some talent.”

That summer of ’69, Lasky worked at Charles Wintour’s
Evening Standard
as an assistant on the “Londoner’s Diary” gossip column. While Anna idolized her father, she never wanted to work for him.

Anna, meanwhile, was playing Miss Homemaker for the first time, while Bobroff was downstairs in his studio with models prancing around him whom he shot for fashion layouts in newspapers and magazines such as the trendy
Harpers & Queen
. “Stephen loved being surrounded by the party
scene,” asserts Lasky. “He loved the glamour, the celebrity, being around gorgeous women.”

The whole scene was like the setting for Antonioni’s 1966 film
Blow-Up
, in which David Hemmings portrayed a hip British playboy photographer, and the milieu gave Anna an insider’s view of that wild, mod sixties London fashion zeitgeist.

And at one point, Anna jumped at the opportunity to be one of Bobroff’s models. For him, she had let her bob grow so her hair, for the last time ever, was shoulder length, thick, and brown, with the ends modishly flipped up. She posed in a variety of cute outfits, including very short and skimpy skating skirts. “She looked really lovely, at her best, the waiflike look, which was very in,” says Lasky. “I remember the photos vividly because they appeared in a black-and-white fashion spread in one of the London newspapers.” It was the second time Anna is known to have modeled for a fashion layout that was published. A year earlier, she and Lasky posed in the teenybopper magazine
Petticoat
, edited by Audrey Slaughter, the woman who would become Charles Wintour’s second wife. Anna and Lasky appeared in a two-page spread, wearing fashionably skimpy dresses and shoes that were far too big; the stylist had to stuff tissue paper in them so the girls could stand comfortably.

Anna’s live-in relationship with Bobroff lasted less than a year. They were still together when Lasky returned to America for her sophomore year at Rad-cliffe in September 1969, but by the time she came home to London at Christmas, it was over, and Anna had returned to her bachelorette digs at Phillimore Gardens. She never spelled out for Lasky why the love affair had ended.

Some years later, the gossipy magazine
Private Eye
, which would go after the Wintours vigorously through the 1970s, described Bobroff as one of Charles Wintour’s “putative son-in-laws.”

Bobroff, who was said to have gotten out of photography, remains mum on the subject of his relationship with Anna Wintour. “I would prefer not to say anything about that time, not to talk at all about her,” he states. “It’s easier that way.”

A
t a party in the latter part of 1969, Anna met and fell for Richard Neville, a twenty-four-year-old shaggy-haired, tall, thin, good-looking, and bright
Australian underground journalist. Down under he had started a successful hippie newspaper, and his goal now was to establish the first such rag in London, called
Oz
, and shake up the Establishment. In the process, he would become both famous and infamous, with friends and supporters the likes of John and Yoko.

By the time Anna set her sights on Neville, he was being fawned over by rich liberals, trendy media types, and chic poseurs. Neville had become more than just an underground newspaper editor on the make; he was considered
the
expert on London’s counterculture and was a regular on BBC television panels, so he was no stranger to tuned-in Anna.

One could practically hear the twang of Cupid’s bow when their eyes met, the way Neville tells it. “I was struck by her egg-white skin. Hailing from the country of bronzed Anzacs, she was a rare sight. Anna was unusual. She had that fringe that just made her slightly alluring, like a silent-film star. She was almost mute, but she had an entrancing quality.”

It also didn’t hurt, Neville freely acknowledges, that her father was the editor of the
Evening Standard
. The newspaper published the first stories about his arrival in London and his publishing plans, and later supported
Oz
and its founder when they got into trouble with the authorities.

When they met at that party, Anna, twenty, was on the arm of a friend, the older, more traditional journalist Anthony Haden-Guest, a member of Nigel Dempster’s dazzling, hard-drinking crowd. “Anthony was one of those people with a great sense of social curiosity,” observes Neville. “He would turn up at upper-class things, but he loved to slum it with the counterculture.”

Anna and Neville met a few times by chance after their introduction. “She would arrive at various parties, where there were the more trendy, groovy journalists, the ones always at the right soirees,” says Neville. Unlike other women he knew, Anna acted and looked different, always chic and elegant. “She didn’t dress like radical counterculture people,” he notes, “and she didn’t dress like Mrs. Main Street, either. She wore high heels, stockings, smart little jackets. I wasn’t at all interested or knowledgeable about fashion, but she always had a look.”

Like the other men she’d been involved with, Neville found Anna shy, and he noted that she had few friends, most of them men.

“I think of her as in the singular. She wasn’t a powerful, gregarious
woman by any means,” he observes. “She was more introverted. I’m a very noisy person and she was a very quiet person, and often noisy people think that quiet people have more going on inside—you get attracted to what you imagine might be depth.” However, he soon discovered, “she didn’t have great depth but was kind of street sharp.” And he couldn’t get a take on her values. “She was still cruising around, unformed. A lot of what happened to her later on [with her career] took me by surprise.”

They became fast friends and then lovers, he says, using the bedroom of her flat at Phillimore Gardens, sometimes after having dined with the Win-tour family upstairs. There was a hitch, however, to going public with their relationship, a big hitch. Neville was living with his beautiful longtime girlfriend in a basement flat with a double mattress in the corner of the front room, in a funky section of Notting Hill, within walking distance of Anna’s. As Neville acknowledged, “My girlfriend and I loved each other, [but] I was more in love with making a splash than with trying to make a relationship work.”

He says Anna was aware of his live-in relationship but was most willing to share the spoils.

“We had a very clandestine, discreet affair,” reveals Neville. “Looking back it was just a strange relationship, going back to her house because I couldn’t really have her in my house for obvious reasons. Anna’s place was a safe abode.”

Occasionally, when his live-in girlfriend wasn’t around, Anna arrived at the sometimes cannabis-beclouded
Oz
office late at night in her trendy Mini with darkly tinted windows to watch Neville and his cohorts put together the next issue. Besides sleeping with Neville, Anna had a burgeoning love affair with what she saw as the creativity of the underground press. “I’m not sure whether Anna knew what her media destiny was going to be, or even what her ambitions were, but anybody with a bit of curiosity about what youth was saying gravitated towards the underground press, and Anna did that,” says Neville. “She had a curiosity about the direction of youth culture.” At the
Oz
office, she flipped through stories and sometimes played editor, making astute critical comments about overdramatic writing or finding a badly written, repetitive piece. “You’ve used the word ‘empirical’ twenty-five times. You should fix it.” Neville respected her opinions.

He became a frequent dinner guest of Anna’s at Phillimore Gardens,
where he saw the family dynamics up close and personal. Her parents were aware of their intimate relationship. Often after dinner the two adjourned to her basement flat for lovemaking. “Anna was given her privacy and her parents were discreet.” Unlike Piers Paul Read, Richard Neville felt that the permissive atmosphere at the Wintours’ was way cool.

But like so many others, Neville noted the chasm that existed between Charles and Nonie Wintour. “Like oil and water,” he recalls. “I never imagined them as a sort of fusion. Nonie was kind of very informed and alert, but I just think Charles was bored by it all. There was a certain deadness between them, emotionally. And that’s just at the table.”

At one dinner party, the talk centered on the legacy of colonialism in Latin America. Anna was bored to death. Among the guests was Charles’s much-admired Maureen Cleave, who had gone off staff at the
Evening Standard
and was just back from Peru with her husband. Also present was Anna’s sister, Nora, whom Neville described as “a dour and fervent Marxist, Marxist and very serious. She wanted to talk about Gronsky and Marx, and the labor movement in Chile, and Anna just wasn’t interested. Anna was pop oriented. Intellectually and physically, Anna and Nora were opposites.”

Involved with Neville and the psychedelic counterculture scene, Anna decided at her hairdresser friend Leslie Russell’s suggestion to experiment with her classic bob. “Around that time, we started to do a lot of crazy colors, like Elton John had pink hair and green hair. People were getting extraordinarily bright blue colors and greens and pinks,” says Russell, who also began cutting Neville’s hair. “Anna was always looking for new ideas and new fashions, and she had a really good eye for it. I gave her this sort of two-dimensional haircut, like two bobs in one. It was actually easier to use two different colors to get the same effect, but Anna kept her own color. She loved the cut, was always ready to have something new.”

The intimate part of Anna and Neville’s affair was short-lived, lasting less than a year, says Neville, who later told a confidant, “Anna and I, we were not the hottest thing in London. There was a moment of intensity, like an exploding firecracker, and then we became friends.”

In 1971, after a highly publicized investigation and trial, Neville and a few of his cohorts were convicted of publishing obscenity in
Oz
. He was sentenced to fifteen months in prison, spent some time behind bars, but his conviction
was quickly reversed on appeal. At one point John Lennon came to his aid, telling Anna’s father’s paper, “Yoko and I have proposed marriage to Richard Neville so he can’t be deported.” Throughout the case, the
Evening Standard
stood behind Neville, and Anna was active in rousing support for him. Their friendship continued for years.