In fact, Alex Walker believes that Anna’s decision to copy Cleave’s hairstyle was, indeed, psychologically complex—more than just her desire to be in fashion. “Charles revered Maureen, Charles was Maureen’s mentor, and Anna desperately wanted Charles to cherish her, too,” he maintains. “It’s quite complicated, but I’m sure Anna wanted to be able to say, ‘Look at me, Daddy. I look like Maureen.’ Anna always desperately—desperately—sought Mr. Wintour’s love and attention, and he wasn’t always there to give it.”
Wintour wanted a hipper, younger readership, and twenty-three-year-old Cleave, an Oxford graduate with a degree in art, was given the youth page beat—the same with-it demographic that Anna later targeted, likely on her father’s advice, when she first became a fashion editor.
“Charles ran many of his ideas for me through Anna because she was keeping her eye on [trendy] things,” Cleave says, looking back. “She was a hip kid, so to speak. I got in trouble once for not knowing the difference between ‘hip’ and ‘hep.’ Anna obviously told her father about that. I’d written the wrong word and Charles said it should be the other word. I knew he’d gotten the correct one from Anna.”
Cleave had virtual free rein to cover the smashing rise of swinging London. The nonpareil Maureen Cleave interview became dinner table and cocktail party conversation.
Her biggest score came when she got a tip from a friend in Liverpool. “She said to me, ‘I hope you realize there’s a lot going on here. There’s this group called the Beatles.’” The quartet had recently cut their first single, “Love Me Do,” and had signed a five-year contract with a manager named Brian Epstein.
Cleave ran the Beatles story idea by Wintour, who asked Anna whether she had ever heard of them. Of course, she told her father, they’re fab. The next day Cleave headed north, thinking she had an exclusive, but was disappointed when she arrived to find a competitor on the scene from the Daily Mail, who had also gotten the word to check out John, Paul, George, and Ringo—known as “the Fab Four”—and this new Mersey Beat.
The gentleman from the Mail didn’t have a chance, though. Lennon preferred Cleave as their interviewer, which she attributes to her bob. “I had a fringe like the Beatles. They liked me from the start because of my hair. I guess they felt we could relate.”
Beginning on Thursday, October 17, 1963, and continuing for three days, the first major interview with the Beatles ran in Charles Wintour’s Evening Standard. That same day the Beatles were at the Abbey Road Studios recording what would quickly become their first American number one hit, “I Want to Hold Your Hand.”
Cleave’s series, pushed by Anna’s highly competitive editor father, who ran the story idea by his with-it teenage daughter who kept her eye on who and what was in and out, had helped to catapult the most successful singing group in music history.
Anna’s bob had helped, too. If Cleave hadn’t been wearing it, the Beatles might not have been so friendly and open, and she might not have gotten their story. In any case, it didn’t hurt.
In its 1963 incarnation, the bob was the brainchild of Vidal Sassoon, who had a shop in posh and fashionable Mayfair that had catered for centuries to London’s upper classes and royalty. Sassoon’s guinea pig was the fashion designer and sometimes model Mary Quant, the epitome of the with-it, mini-skirted swinging London chick. She was thrilled with the cut and decided to have all of her models given the bob by Sassoon. A British Vogue editor, attending Quant’s show, was overwhelmed. “At last,” she wrote, “hair is going to look like hair again.”
Other trendy haircutters soon jumped on the bob bandwagon, such as Leonard of Mayfair, where Leslie Russell gave Anna her very first bob. “Anna was about fourteen, fifteen when she came in. She had hair way past her shoulders, like Jean Shrimpton’s. She said she saw photos in [British] Vogue of some cuts that I did, and I remember she came in with a picture she’d torn from Vogue. And so I cut her hair, and it was the haircut of the time, which everyone was getting—the straight hair, the long fringe, the same bob she has today.”
Mainly, Anna chose Leonard of Mayfair over Sassoon because two of her idols got their bobs there—Maureen Cleave, and a kicky nineteen-year-old former ten-pound-a-week secretary named Cathy McGowan, who overnight jumped to the forefront of the British pop revolution as the trendy host of a top-rated music television program Ready, Steady, Go!, Britain’s version of American Bandstand. Virtually every teen from London to Liverpool—and Anna was no exception—tuned in early on Friday evenings, 6:07 P.M., to be precise, before they went out clubbing. The show’s energized motto was “The Weekend Starts Here!”
Teenage Anna adored Cathy McGowan, who wore the trendiest boutique fashions and the latest makeup styles, and featured the jargon, the attitude, and the sensibility of mid-sixties happening London. Anna would come away from the TV each week knowing what to buy, where to buy it, and how to wear it.
“Cathy was a client of mine,” Leslie Russell says. “She had the bob, and Anna had read in a magazine or a newspaper that I’d cut Cathy’s hair, and that was another reason for her coming to me. It suited Anna perfectly. And still does. She’s got those nice cheekbones, which looked perfect for that look of the time. Certainly in those days she had perfect, shiny, thick light brown hair, very good hair to hang straight, with a bit of blow drying to turn the hair under a bit. Anna was very sixties looking.”
Scores of super birds and dollies passed through Leonard of Mayfair in those days, but Russell never forgot Anna’s look: short, short miniskirts; low-heeled, pointed shoes; tight tank tops; and very little makeup—“some eye shadow and mascara, but that was about it. She was not red lips and caked up. She didn’t need it.”
Besides going to Leslie Russell to have her hair cut, Anna paid particular attention to the health of her tresses and began getting scalp treatments and buying special-formula hair products from a bespectacled man named Philip Kingsley, who took hair quite seriously. He originally planned to become a doctor, but visits to his uncle’s hair salon got him interested in hair care. Instead of medical school, he became certified as a trichologist, an expert in hair and scalp problems. In the early sixties, he opened a one-man practice in London.
“Charles Wintour originally came to see me as a client because his hair was thinning,” Kingsley says. “And he saw me throughout his life. He told Anna, ‘You should start taking care of your hair when you’re young.’ When Anna first came to me as a teenager, she didn’t have very much wrong, but I started treating her, too. I get people’s hair in the best possible condition, and then they can do what they like with it. It’s like going to a doctor.”
Over the years, Anna dutifully used Kingsley’s shampoo, containing a formula based on the texture of her own hair, along with his exclusive hair tonics and conditioners. Kingsley also recommended that she take a lot of yeast tablets, but they caused constipation.
After Anna moved to New York in the mid-1970s to begin her climb to the summit, she continued seeing Kingsley, who had opened a practice there. Kingsley believes that stress is bad for hair, and as Anna rose in the high-pressure fashion magazine field, jumping from one anxiety-ridden fashion editor’s job to another, her stress built up and she required his help.
“How often I saw her depended on how stressed she became,” Kingsley reveals. “Her hair didn’t behave as it ought to have done when she was under stress, and sometimes Anna was under more stress than others.” Kingsley made a chart for Anna’s good and bad hair days, and every so often reassessed the health of her hair, depending on the highs and lows of her anxiety.
Anna was among Kingsley’s first clients—a celebrity list that grew to include Cher, Jerry Hall, Mick Jagger, Ivana Trump, Sigourney Weaver, Kate Winslet, Candice Bergen, and Barbra Streisand, among others.
Besides her hair, teenaged Anna worked hard at maintaining her skin. She read voraciously about ways to fight pimples, acne, and blotches—and how to deal with other teenage girl problems—in her gospel, the American magazine
Seventeen, copies of which she borrowed from Vivienne Lasky, who had a subscription. Convinced she was going to have bad skin, and obsessed with keeping it clear, she went weekly to an exclusive salon on Baker Street, fancier than Elizabeth Arden, to get facials and was no doubt their youngest client.
“Her skin was fine,” Lasky points out, “but she went to the salon every week for prevention.”
While Anna was sleek and chic, she was harshly critical and sarcastic, and spiritedly made fun of people who weren’t. “Anna really cared about appearance. She would point out another girl and say, ‘My God, look how fat she is . . . look at her face . . . look at thatgirl’s horrible, curly hair,’” recalls Lasky, who had curly hair and became at times the target of her best friend’s biting tongue. Although both wore glasses—Anna’s were expensive tortoiseshell granny glasses—she ridiculed Lasky’s poor eyesight. “Anna didn’t wear her glasses all the time,” Lasky says. “She could manage very well without them, although sometimes she’d ask me who somebody was across a crowded room. But she’d be very critical of me and bitchy when we’d go horseback riding or play tennis because my eyesight was so bad. I had trouble seeing the ball. I couldn’t ride as fast as her. She could be mean like that.”
From the time she was a teen, Anna was brusque and snarky—traits she inherited mostly from her father but also from her mother, who was known for her critical and sarcastic manner.
Anna’s nastiness appeared calculated and was offensive, which made Lasky and others who were her targets feel terrible.
“If I disliked anything about Anna when we were kids,” Lasky offers, “it was her rudeness on the telephone. Her entire family did it—they never said good-bye. They’d just hang up on you. With Anna, I knew it was coming. ‘Well, I’ll see you.’ Click. No good-byes.
“My mother would say, ‘It’s the rudest thing, no civility’ And my mother loved Anna. I confronted her. ‘What is it with this not saying good-bye?’ And she said, ‘Well, there’s no point, is there, really? We’re finished talking. How can you feel bad about that?’ And I said, ‘Nobody else does that. If you want to make friends with people, they’re going to think it’s odd. You’re the only person I know who does that.’ She didn’t care.”
There were even worse slights that left Lasky hurt and with a sour taste, both about herself and their friendship. Unlike Anna, Lasky was an eater, and Anna gloated over the fact that she always stayed thin. For instance, Anna bought little gifts of clothing for Lasky. But there was always one major hitch. Everything was thoughtlessly too small, including a custom-made Regency ball gown with lavender and white stripes that Lasky could barely squeeze into.
“My mother noticed these things. She always used to say, ‘How could your best friend buy you something and it’s always a size too small?’ That dress Anna bought me, I couldn’t get into the damn thing because the arms were so tight.” Another time, Anna bought Vivienne an expensive patchwork quilt skirt at Liberty’s, one of the grandes dames of London department stores. “Like everything else, it didn’t fit,” she says, “I think I squeezed into it once.”
Lasky’s mother was a Prussian former ballet dancer and model, an exotic cross, according to her daughter, between Audrey Hepburn and Greta Garbo. Brigitte Lasky, who converted to Judaism for her Jewish husband and became a U.S. citizen, was a fashion plate with whom Anna bonded, spending almost more time with Mrs. Lasky than with her own plain-Jane mother, who was preoccupied with her social work. “Anna was especially crazy about my mother,” offers Lasky. “She thought she was the cat’s meow and saw her as a role model.”
Nevertheless, Brigitte Lasky felt that Anna bought the small sizes purposefully and maliciously to tease and taunt her daughter. Unlike Vivienne Lasky, who was a tad plump, Anna was skinny, but she was big-boned and usually had to buy larger sizes for herself and have them taken in. While Lasky thought Anna looked “great” in certain things, such as later in Chanel, she felt she looked “awful” in evening dresses then and now, “because her elbows, wrists, and knees are too big. She’s like Calista Flockhart and Lara Flynn Boyle. It can look painful.”
Anna knew that juicy, thick lamb chops were her pal’s favorite. She even taught herself to cook them to Lasky’s taste, so she could gloat while she watched her clean her plate. “Anna would make my favorite food. Then she would just sit there and watch me eat. She wouldn’t eat, or she would just pick, and she’d point out that I was ‘pleasantly plump.’ I said, ‘Well, Anna, I don’t want to be a model,’ and she said, wagging her finger, ‘You know, Vivienne, we don’t want to get too pudgy’ My mother says I would always come home from those dinners feeling a lack of self-esteem. She said I didn’t come back confident and smiling.”
Anna hurt her friend’s feelings by making fun of her weight and putting her on the spot by demanding, “Why don’t you have more self-control?” Lasky’s meek response was, “ ‘Life is too short . . . dieting all the time makes me crotchety.’ Well, that sends a message. I wasn’t so stupid. My mother always said, ‘Anna invites you to dinner, makes your favorite food, buys your favorite cheesecake, and she’s flitting about, but did she eat anything?’ I said, ‘Mom, you know she didn’t.’ My mother thought she was malicious. I’d say, ‘I don’t believe that of her. She loves me. She’s my best friend.’”
As one of Charles and Nonie Wintour’s favorites on the Evening Standard’s staff, Alex Walker often socialized with his editor. He was invited to their cocktail and dinner parties—Charles specialized in mixing a martini that left guests reeling—and was an overnight guest at their country place in West Farleigh, a village in Kent. And he got to know teenage Anna, who, he noted, was an “absolute monster” who “didn’t mind insisting on [her] own views on whatever anyone else said, particularly in that family.”
Walker thought Anna would do or say things just to be mean. He says he thought of her as a complex amalgam of such wicked film characters as The Bad Seed’s Rhoda Penmark, Mildred Pierce’s Vida Pierce, and All About Eve’s Eve Harrington. As a movie critic and a serious biographer of Hollywood greats, Walker enjoyed film analogies, even if possibly exaggerated.
“I’d stay with Charles and Nonie for the weekend,” he recalls. “I suppose Anna was fourteen, fifteen, and she had a horse. I’d hold the long harness while I delicately led her around, rather than galloping around, the paddock. When she was through riding, she’d say, ‘I think I’ve had quite enough of this, Mr. Walker. Now help me down.’ I was struck by the fact that she was very, very mature—far more mature than her age. The future editrix was in the blood there, that’s for certain.”
Anna was crazy about riding at that time, and she made a serious pitch to her father to quit his powerful job at the Evening Standard and. take over editorship of the local Kent Messenger so that she could enroll at the local stables with thoughts of becoming a chic, miniskirted veterinarian.
“Even as a child she had her father’s coldness,” continues Walker. “She was very much like her father. Anna had a self-possession that was beyond her years. She was in fact more than self-possessed. She was patrician. She was not a playful child. Her behavior manifested itself in quite small ways back then—simply in being stiffly polite but not taking very much notice of you. What she did, she did with purpose.”
But Anna had no tolerance for rude behavior that intruded upon her life and was especially upset with people who were tardy. “Anna could be very impatient,” Vivienne Lasky emphasizes. “She was actually a perfectionist. In that way she was sort of a Martha Stewart–ish person, always in control. To Anna, the thought of anyone being late was terribly rude, and she cut off people if they didn’t arrive at precisely the specified time—at least not anyone terribly important to her. ‘Well, we’re not going to meet them again, that’s that,’ she’d say with finality. ‘They’re not reliable. We’ll just go on our own. What’s the point of meeting people if they show up late.’”
four
A Growing Independence
Around the time Anna turned fifteen, in 1964, the Wintours decided to move from their bland contemporary town house in St. Johns Wood. The uninteresting house no longer fit the regal image of the editor of a serious London newspaper.
Anna especially hated her tiny bedroom, though all of the rooms in the house were small. She felt hers was babyish-looking, and just prior to the family’s purchase of the new house she redid her room in an elegant green, faintly striped wallpaper.
In general, the house held bad memories because of the death of the Win-tours’ firstborn.
Vivienne Lasky had always found it odd that all of the windows in Anna’s room and those of her siblings had bars on them, which in those days was a rare addition in most British homes. One afternoon, sitting with Anna, she asked her about the guarded atmosphere, and Anna’s response surprised her. “My mother’s paranoid,” she stated, “that one of us is going to fall out.”
When Lasky asked her why, Anna revealed the sad story of her brother’s death and said that her mother still feared that the worst could happen to another of her children. “Anna said Nonie was edgy, nervous about the children’s safety, that one of them might stand on a footstool or a chair and fall out”—thus the prisonlike bars. “Anna never talked about him again, and I never heard anything about the dead brother from other members of the family. But neither Anna nor any of the other children were permitted to ride or had bikes.”
The Wintours moved to an elegant late-nineteenth-century four-story white stucco home at 9 Phillimore Gardens, in fashionable Kensington, close to the area’s fancy department stores and antiques shops, a neighborhood “still stuffily grand at that point in time,” observes Valerie Grove. “Grandeur and wealth was the keynote.” It was a fine family house for entertaining, with a large garden, immediately adjacent to bucolic Holland Park. Compared to their previous home, the Wintours’ new house was enormous: nine bedrooms, four bathrooms (one en suite), three reception rooms, many fireplaces (the mantels of which were stolen during the renovation), a kitchen and breakfast room, and a cloakroom, all high-ceilinged with beautiful moldings. The facade had eight windows that faced the street, flooding the front rooms with light.
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