“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.”
At 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.
nine
Making the Masthead
The education of Anna Wintour as fashion magazine editor began with the dawn of the glitter, glam, and disco seventies at Harper’s Bazaar, once Britain’s premier couture monthly. It was in the process of becoming hipper by merging with a magazine called Queen, which had become the irreverent, witty, and trendy fashion must-read of swinging London.
With the deal in the works, the word had gone out: The combined magazine was looking for new hires, especially a fashion assistant, the lowest-paid job in the business. But Anna didn’t need or care about the paycheck. She was far more intrigued with being around hot fashion, cool people, and a hip environment.
In early January 1970, she arrived at the magazine’s offices for an interview with the editor, Jennifer Hocking, a former model who was a bit in the dark about the identity of this fabulous-looking fashionista, sporting Missoni, with the fringe over her eyes.
“When I took her on I had no idea who she was,” recalls Hocking, who, because Anna looked so young, thought she was about seventeen. “She said something about her father being a journalist, and as I can never remember anybody’s name, it didn’t connect with me that he was the Charles Wintour.” Hocking also wasn’t aware that it was Wintour, working behind the scenes, who got Anna in the door.
But she was satisfied that this new girl could work out. Anna struck her as quite reserved, had an extraordinary look, and, unlike other girls she’d recently interviewed, had neither asked nor cared about company benefits. She didn’t know at the time that Anna—unlike Hocking herself, who made most of her own clothes—had family money.
“We weren’t looking for anyone sensational,” Hocking continues, “just someone who would work well with other people and get on with it.”
Besides, the fashion department was a very small part of the magazine, which was more generalized in those days. The department took up a very small area at the end of the office, with a closet for clothing and other accoutrements. As Laura Pank, one of the editors, notes, “Fashion was kind of a bit that we had to tolerate. The editorial was much more important.”
And so Hocking hired Anna, who had even beaten out an applicant with more experience from British Vogue.
Years later, Anna said her start in the fashion world was virtually predestined. “I think being Charles Wintour’s daughter probably got me my first interview and my first job.” She also boasted that she had bluffed her way through the interview—something Hocking hadn’t caught—by claiming she could handle fashion shoots, though she had no prior fashion magazine experience. Well, she did have a little. Having lived with Stephen Bobroff, who had shot for Queen, and having modeled twice before, and having posed as a trendy bird in London’s hottest clubs since she was a teen as part of her nightlife world, Anna probably knew a bit more about what was required in a shoot than the next girl in line.
Modestly, she later asserted that she didn’t see a future for herself in the world of Harpers & Queen. “I just sort of fell into magazines,” she maintained. “So much of what happened to me has happened by chance. There was no master plan. . . . This was a time when the fashion magazines were widely regarded by one’s mothers as finishing schools for girls of a certain background and a certain name. One had fun there, but one dabbled in the business in anticipation of marriage and, all being well, a large house somewhere in the English countryside.”
But that’s not the way Jennifer Hocking viewed what she quickly saw as her “very clever, incredibly organized, so together, quietly driven, sometimes terrifying” new hire.
Anna’s name first appeared far down on the masthead as one of three fashion assistants in the March 1970 issue, whose cover featured “The Anne Bo-leyn face, a summer tanned image of Elizabethan beauty.”
She had landed on her feet her very first day on the job and never stopped running and never looked back to see whom she left in her dust.
; The Wintour girl didn’t strike Hocking as a dilettante, as were some of the others on staff. From the beginning, she saw someone “driven, determined, and ambitious.” Anna’s coworkers endured her—some with awe, others with contempt, and still others with fear and alarm.
“She had this incredible brain, and I used to think it would be amazing to meet her when she was thirty-five, because she was too mature for her age,” observes Hocking. “She was so organized. She would make business appointments for lunch when the rest of us were sort of sitting around twiddling our thumbs. She was just so together. With most young people, it’s, ‘Oh, I forgot this, I forgot that.’ There was none of that nonsense. She was very quick at picking up things. If you said something to her, you knew she’d taken it in because next time she was talking about something, she’d say, oh, such and so, and I’d remember, I told you that. Just extraordinary.”
Willie Landels, a creative, perceptive, and gentle man who had been promoted to editor but handled the duties of art director at the same time, felt from the first day he was introduced to Anna that her ambition was obvious, that she was very determined to succeed. “There were other girls,” he notes, “who were more talented, who had amazing taste and were chic, but didn’t have that incredible drive that Anna had—like a businessman who is really successful, who only looks in one direction and goes for it. Anna had that—this total conviction that she was aiming for the top job.”
But Landels had his qualms about her, too. “She had very precise ideas about clothes, a very good sense of quality, but nothing adventurous, always rather conventional. I didn’t see her as being very original, but was very much in the mainstream, which made her right later for Vogue, which was hardly revolutionary. Her intelligence? Well, obviously she’s no fool. People like Anna who are so beamed at something have an intelligence that is highly developed in one direction. The whole energy goes into one thing. In her case it was succeeding.”
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