“Nonie and Charles really did like their children, and they were much admired by them. But there never was a particularly cozy family feeling because Charles’s mind was always inevitably elsewhere. You can’t edit a paper like the Evening Standard and have your mind focused on whatever Anna wants to do in the afternoon. That didn’t exist,” observes Drusilla Beyfus Shulman. “I won’t say Charles was an absentee father, because he was certainly concerned about his children, but he was at his desk very early in the morning, was there all day, dining out with people in the evening. He didn’t have a lot of time left over for Anna.”
Anna found a surrogate of sorts in Vivienne Lasky’s autocratic father, the esteemed Melvin Lasky, who wasn’t an easy man to spend time with because he could be horribly caustic and cutting.
But Anna? Anna was tops in Lasky’s book. He used all of his charm around her, probably because Anna was reverential and worshipful—she naturally knew how to handle men and their egos—and appeared captivated and enchanted with his stories about the celebrities he knew and the instantly recognizable writers like Mailer and Eliot and Auden and other big names whose pieces he edited and corrected. Anna’d sit at the table seemingly spellbound but sometimes peppering him with questions. Did he know this person? Had he met that person? Do famous writers ever object to your correcting them? Anna knew that her own father’s style was to keep hands off his reporters’ copy unless absolutely necessary. “Some will ask, ‘Did you change anything?’ ” Lasky told her. “Anna, you have to make them feel that that’s the way they wrote it.”
While the Wintours gave Anna an extraordinary amount of independence—her own apartment, freedom to date older men, clubbing until all hours—Charles and Nonie’s prime concern was over her disinterest in school as underscored by her attitude at North London Collegiate. Charles, from Cambridge, and Nonie, from Radcliffe, were educational elitists and wanted her to graduate and go on to a proper university. The Wintours had planned for Nora, Patrick, and James—all academic high achievers—to receive Oxbridge educations and had started putting the pressure on Anna. “I remember them discussing it with Anna, telling her, ‘You’ll be the first not to go.’ Of course they expected her to follow in their footsteps,” Vivienne Lasky says.
“Charles was the great brain of the family,” notes Drusilla Beyfus Shul-man, “and Anna was, well, pretty. As the great brain of the family, Charles always took a rather skeptical view of Anna’s intellectual capacities.”
In 1966, the Wintours’ tug-of-war with Anna over her schooling became a moot point. About to turn seventeen, Anna had had it with North London Collegiate. It would be a piece of clothing—the miniskirt—that helped bring down the curtain on her formal education.
When Anna was nabbed for small infractions during her three years at North London, she usually got off the hook, mostly because the headmistress, Dame Kitty Anderson, was a friend of Charles Wintour’s brother-in-law, Lord James of Rusholme, a noted educator. Because of Dame Kitty’s ties to the Wintours, Anna felt a sense of entitlement. But all that changed when the headmistress retired in July 1965 and was replaced by Madeleine McLauch-lan, who proceeded to make life miserable for Anna. “She was cold and hard,” recalls Lasky, “and acted like she had a stick up her ass. The whole school changed. It became very tense. Tests were given that no one passed. Everybody felt insecure.”
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.”
seven
Finding Love at Harrods
In 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.
Anna 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 wa
s 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.
eight
Live-in Model
Vivienne 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.
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