Front Row

by Jerry Oppenheimer

  She always made a showing at the Ad Lib, near Leicester Square, which had a reputation as being a hangout for the hottest dollies in London, a club where virtually everybody in the balcony overlooking the dance floor was toking up.

  Anna didn’t do drugs, even though marijuana, cocaine, LSD, and everything else one could snort, inhale, or shoot to get recreationally high was all around her, everywhere she went.

  “Anna was always too much in control to be interested in drugs,” Lasky maintains. “She was hideously healthy” She says Anna didn’t even drink at the clubs, but nursed Coca-Colas, though she wouldn’t turn down Veuve Cliquot if offered by a gentleman.

  Anna often went off to Dolly’s, on Jermyn Street, which drew a hip crowd of journalists and rockers, and she was a regular at the very exclusive London discotheque called Sibylla’s, on Swallow Street near Piccadilly Circus, which became known as the Beatles’ disco because George Harrison owned a small percentage of the place. The club’s private preopening night was unforgettable, with an elite boldface list of celebs: all of the Beatles, the Stones, Cathy McGowan, Julie Christie, Mary Quant, among other London fixtures. It was the kind of place where the owner felt it was successful only if you couldn’t get in, making it Anna’s kind of place, and she was there with Nigel Dempster for the premier.

  “At fifteen, sixteen, Anna had this downtown London life,” Lasky says. “London was a hotbed of clubs, concerts, and endless parties. She went where it was fashionable to be seen and to see people. She didn’t need much sleep. She had enormous energy.

  “She liked clubs and clubbing and dancing more than she liked the Beatles or the Stones. Anna didn’t go to rock concerts and didn’t go gaga over anyone in pop music.”

  But Anna did once become mad for a sexy star in his late fifties, more her speed—the actor Laurence Olivier, whom she saw in Shakespeare’s Henry V at least a dozen times. While most girls Anna’s age were chasing Mick and Keith, she began pursuing Olivier. She often skipped school, bringing a satchel of clothing with her, changing out of her ugly North London Collegiate uniform and into something sexy in the ladies’ room of the underground station near the office building where Olivier had his production company. She’d stake out the lobby and wait for hours in hopes of meeting him. This went on sporadically for months, but she never was successful, and she finally gave up her quest.

  Nothing seemed too risqué for sixteen-year-old Anna, who became delicious arm candy for Dempster, who once boasted that his nubile girlfriend’s breasts were “large” and “quite delectable.” When the London Playboy Club and Casino, the five-story swingers’ paradise, had its star-studded opening night party, overseen by Woody Allen as a favor to Hugh Hefner, on July 1, 1966, Anna partied the night away with Dempster and hundreds of other sybarites, hedonists, and celebrities who had turned out for the festivities. As Vivienne Lasky notes wryly, “She’d go to the opening of an envelope.” In this case, though, it was a celebration of half-naked Bunnies spinning roulette wheels and turning cards for oil-rich Arabs, British playboys and their birds, and the usual turnout of Euro trash. The wild goings-on continued through the night at the Playmate Bar, in the disco, and at intimate gatherings in members’ rented private rooms.

  An Evening Standard photographer was there to cover the event and shot photos of Anna shaking hands with pajama-clad Hugh Hefner. The next day a gloating photo editor showed the pictures to Anna’s father. “It did not go over well,” recalled Dempster.

  Charles Wintour didn’t mind Anna having her independence, but he did mind her going out with Dempster. Brian Vine, a onetime New York bureau chief of the London Daily Express, saw Anna and Dempster together at the Playboy Club opening. A few days later, Dempster told him that Charles Wintour exploded when he called for his daughter at Phillimore Gardens.

  “Nigel said Charles was very angry, so I think Nigel had to always hide the fact that they were seeing each other,” recounts Vine. “Charles Wintour was a rather conservative chap and a powerful editor, and he couldn’t think of his daughter going out with this sort of a scurrilous gossip hack. Nigel wasn’t acceptable to the Wintour family.”

  Nevertheless, Anna was enthralled with the glitzy world Dempster opened to her, and their relationship continued on and off, Dempster claimed, for seven years.

  “Dempster likes to suggest that he had [a relationship] with Anna,” asserts London Daily Mail gossip writer Peter McKay. “Dempster tells a story of how he was on a sofa in the drawing room of the Wintour house with Anna one evening when he looked up to see this very unnerving sight of these two scuffed suede shoes beneath the set of doors to the room. Charles [Wintour] had come home unexpectedly, didn’t come in the room, but was standing quietly outside eavesdropping. Dempster says he had to hide it [the romance] from Wintour, who was in a position to get him fired.”

  Brian Vine heard a similar tale from Dempster, with the details tweaked a bit. In that scenario, Dempster said he had to duck into a closet because Anna feared that her father would storm into the room and discover them together.

  Those who know Dempster feel certain that the relationship was not intimate. “Dempster would be frightened because he wanted a career as a journalist,” observes Vine.

  Dempster’s first wife from the early 1970s, Emma de Bendern, who came from a titled background, says, “Anna was very young and Nigel thought she was terribly beautiful. I’m sure it was a dating thing,” she maintains. “Before I married Nigel, he brought Anna to Spain where my mother had a little house on Majorca and I was living there. She came to stay with Nigel for a long weekend. She wouldn’t go in the sun because she had the most wonderful translucent skin and sat under an umbrella so as not to get any light. She was sort of a porcelain doll, absolutely perfectly manicured, very quiet and very unassuming, hiding behind the fringe of her very immaculate bob, and her body incredibly skinny—but with extraordinary, lurking determination.

  “She didn’t seem to have any personality, and I didn’t feel there was any sexuality about her. I just remember Nigel being rather protective, acting like a father towards her. I didn’t feel there was any romance. But perhaps I was just being fooled, perhaps that was a clever ruse to not arouse my suspicions. But if he was having an affair with her, there was no vibe. It didn’tfeellike it.”

  If anything intimate was going on, one would have expected Anna to confess all to her best friend. But she remained mum. “Anna never talked about sex or relationships, ever,” says Vivienne Lasky. “We were not Sex and the City girls. And Anna’s very British, very private, and she’s not touchy-feely. She’d never talk about what happened between her and a man.”

  By 1971, Dempster had moved from lowly legman at the Daily Express to second in command under Paul Callan, who hired him to work on his new Daily Mail “Diary” column. Callan quickly realized he had made a major mistake hiring Dempster, who tried to steal his job. According to one report, “Dempster knifed him. It was classic stuff. He kept all his decent stories until Callan was away, then produced them in a way that made Callan look second rate.”

  Whatever Callan might have thought about Dempster’s career manipulations, Anna is said to have respected his cutthroat methods. They shared a similar philosophy: “Get to the top any way you can,” a journalist who knew them both says.

  six

  Shopgirl Dropout

  If there is a singular, defining moment for young Anna Wintour, it might have been the day her father summoned the Evening Standard’s fashion editor, Barbara Griggs, into his office and said, “I wonder if you could do me a great personal kindness?” Griggs, who had been covering fashion for years and had once worked at British Vogue, said, “Charles, I’d be delighted. What can I do?”

  Sounding a bit uneasy, he said, “Well, my daughter Anna thinks she wants something to do in the fashion world. I wonder if you could take her out to lunch and give her some advice. I’ll pay for the lunch, of course.”

  Looking back on that moment years later, Grigg
s remarks, “I don’t think that Charles was big on fashion, and I don’t think he wanted that for his favorite daughter. He hoped for more for Anna at that point.”

  Griggs invited Anna to lunch and found herself sitting opposite “this incredibly self-possessed child—extreme self-possession, which is unusual in someone of her age.” She found Anna very focused and came away from their meeting thinking that this girl would go far. “It appeared to me that she needed absolutely no advice from anyone, and she’d carve her own path fairly smoothly.”

  The next day, still following through on her editor’s request, Griggs telephoned Barbara Hulanicki, the owner of Biba, one of the hottest boutiques in London, and asked her whether she had any part-time openings for a very savvy and confident schoolgirl whose father happened to be the powerful editor of the Evening Standard. Anna was a regular customer and wore the styles Hulanicki promoted—knee-high boots, tight tops, and miniskirts—and Vivienne Lasky firmly believes that Anna’s obsession with clothing was strongly influenced by Biba and its fashions.

  The boutique became a glittering star in London’s sixties fashion firmament, influencing the way girls in the street dressed. Hulanicki paid particular attention to the cut of her clothes, giving them a couture look, so every girl who wore her designs was made to look thin. Overnight, Biba’s customer base cut through the class system and changed from strictly working-class girls to include pop stars, actresses, aristocrats, and all the young fashionistas like Anna who wanted the “look.” An expert at promotion, Hulanicki shrewdly designed outfits specifically for influential trendsetters like Cathy McGowan and for the very visible pop singer Cilla Black. Julie Christie wore Biba for her role in Darling. And iconic model Twiggy’s reed-thin frame was always draped in Biba designs.

  Biba’s hot mail-order catalog used photographers like Helmut Newton—a favorite of Anna’s when she became a fashion editor—to produce shots that juxtaposed innocence and knowingness, which, in fact, was the image Anna possessed in the eyes of men during the sixties and seventies.

  As Hulanicki remembers the call from her fashion editor friend at the Evening Standard, Barbara Griggs asked, “Oh, could the daughter of Charles Wintour come and have a holiday job? You know, just to learn about working in a boutique.” Hulanicki said yes immediately—a prominent editor’s daughter as a shopgirl couldn’t hurt business—and hired her to help out on Saturdays and holidays in her Kensington Church Street shop and also at a Biba branch in touristy Brighton on the English Channel. Hulanicki often escorted Anna and few other girls on the one-hour train ride. They spent the day working in the shop, returning that night.

  “Anna would have been about fifteen, sixteen,” Hulanicki recalls, “and was very young, very sweet, very pretty, and very, very quiet, but I had a feeling her intellect was definitely a little bit higher than fashion. Anna came from an educated family and most of the Biba girls didn’t. She was not typical. But she became one of the girls who were learning the boutique business.”

  Hulanicki was intrigued with Anna and kept a close watch on her. While Anna appeared shy and timid, “I could see she was taking everything in,” Hulanicki says. “Anna was interested in fashion, but also Biba was the place to be. Boutiques were the most important places in those days . . . all the girls wanted to work in them.”

  Hulanicki remembers Anna, who was paid about fifteen dollars a day, as being “quite chubby” compared to the other Biba girls, who looked even skinnier than Twiggy. But that may have been because of eating disorders or, worse still, drugs. And most of them were older than Anna, at least eighteen. A number of them lived extremely wild lives: Some became addicts or alcoholics, and others died tragically in a series of auto accidents, probably intoxicated or stoned, victims of the excesses of swinging London.

  Biba was a scene, to say the least.

  Beautiful, tall, very skinny Joanna Dingemann, Anna’s age and also a “Saturday girl,” later a Biba manager, a Paris model, and a fashion school teacher, says that even then Anna stood out from the beautiful crowd—an elegant and, she notes, very furry vision. “She used to wear fur—a full-length fox coat—at a time when it was just becoming unfashionable to wear fur . . . it was just sort of going out of favor, not in a political sense like today, but just in terms of style. But there she was draped in it. Anna went her own way.”

  While Charles Wintour used his good name and influence to get Anna her boutique gig—and it would not be the last time her father’s power would help her up the ladder—his hope then was that Anna wasn’t really serious about fashion as a career.

  “Charles and Nonie thought it was just a phase,” observes Vivienne Lasky. “It was what she expected them to say. Her parents didn’t understand it, but Anna had latched on to fashion with a passion that would endure. By sixteen she was fashion, fashion, fashion all the way.”

  The London fashion revolution had encompassed her. Years later, remembering that time, Anna said, “You would have had to have been living up in Scotland underground to not have been affected by it.”

  Brigitte Lasky gave Anna the kind of encouragement for her fashion passion that she didn’t get at home. Lasky, who wore couture, and Anna talked constantly about clothes and style, the kind of conversations Anna never had with her own mother.

  As a social worker, Nonie Wintour wore thick glasses, shunned makeup, and dressed conservatively—“like a working person, Talbot-sy,” says Vivi-enne Lasky. “Nonie was more like Hillary [Clinton] . . . can’t be bothered, I’ll wear the next navy blue suit. Nonie wore navy a lot.” Later, when she got into fashion magazines, Anna would buy clothes for her mother to make her appearance smarter.

  Unlike Anna, none of the other Wintours had a sense of style, and all dressed plainly. “Anna hated badly dressed people,” recalls Lasky. “We’d sit on Bond Street having tea at some trendy place and she’d comment on all the people. She was very judgmental. Everybody had to be perfect. She criticized their clothes. ‘How can people go out like that? Don’t they ever look in the mirror?’”

  Anna once bought an expensive Dior dress shirt for her brother Jim, who wore it incorrectly, letting it hang out of his trousers. Anna just shook her head and rolled her eyes.

  “For Anna to have come out of that family is amazing,” states Drusilla Bey-fus Shulman, a onetime editor at British Vogue and a Wintour family friend. “They were all terribly badly dressed. They were laughable. Nora’s clothes were pathetic—they were all pathetic. Nora’s a rather plain girl and suffered dreadfully from being a plain girl in Anna’s shadow. She was always the plain sister and Anna was incredibly pretty, always looked wonderful.

  “Right from the age of twelve, it seems, Anna was convinced of the almost psychic power of clothes. When she went off with her boyfriends, age thirteen or whatever, she always looked just dreamy. I remember seeing her in a very shiny white coat and boots, vinyl I guess, and she was going off to spend a holiday in Switzerland. She must have been about fourteen, and she just looked marvelous”

  Shulman says that Anna’s parents never understood her early obsession with fashion. She compares their response to parents who are stunned to discover their son or daughter is a music prodigy. “Where did it come from? Who knows? Why do these amazing qualities emerge? They just do. It came from no one in the Wintour family, that’s for certain. Her secret is natural talent.”

  Because of their close relationship, Anna took Brigitte Lasky into her confidence, one of the few women who ever entered that charmed circle. Shockingly, Anna complained that her mother seemed more concerned about, and loving toward, the foster and adoptive children in her case files than about Anna herself Anna saw her as a mother figure, but not to her own flesh-and-blood children. Anna referred bitterly to the children in her mother’s case files as “Nonie’s kids.” While Anna rarely showed any form of emotion, she clearly felt some resentment toward her mother because she wasn’t more of her focus.

  “It made Anna feel second fiddle,” says Vivienne Lasky.<
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  Lasky, who remained friends with Anna’s mother for years, believes that Nonie Wintour felt absolutely fulfilled because of her social work with children. “Maybe by throwing herself in and saving other people’s children, Nonie was compensating for the loss of her first child whom she couldn’t save.”

  Anna had the same hunger for Charles Wintour’s attention—a father figure and mentor to his staffers at the newspaper but not often there for his own daughter.

  Years later she acknowledged, “When I was a child I was never alone with my father. There were just too many of us. He was the one we were frightened of, but he wasn’t judgmental. He’s discreet and charming in that way, but he notices everything and you know what he thinks all the same.” He was even more tied to his work than his wife. Anna said she didn’t see much of him because of his newspaper and remembered “interrupted holidays” whenever wars broke out or people got killed. Anna complained that her parents were usually out and that she spent a lot of time as a child with nannies and au pairs.

  “Nonie had a work ethic, and Charles had an incredible work ethic,” says Lasky. “They had the same passions for what they were doing and stayed with those passions. Anna has it, too—an extraordinary work ethic.”

  But when Anna did see her father when he was home from the office, or taking time from social engagements, he generated excitement, telling her which celebrity or famous politician had come into the office that day or the big story the paper was working on. He passed on to her the same rush of adrenaline that made him rub his hands together and shout “Hah!” in the Evening Standard newsroom when exciting stories like the John Profumo-Christine Keeler sex scandal came thick and fast as they did in the sixties. He made Anna feel empowered, he made her feel like an insider. She thought it was wonderful getting to know firsthand something that would make headlines the next day.