Front Row

by Jerry Oppenheimer

  In a home filled with so much angst, Anna turned inward, became even more shy and withdrawn, and had no known close friends. At the North Bridge House School in Hampstead she was quiet as a church mouse, a loner who did not stand out from the crowd. It was clear she was horribly affected by her parents’ turmoil. Along with the curtain of gloom that had descended in the wake of her brother’s death, her father, whom she dearly loved, was rarely around, busy devoting his life to Beaverbrook and his success as an editor.

  At the age of eleven, in September 1960, Anna was enrolled at London’s exclusive Queens College, which wasn’t a college at all but rather a fancy middle and high school that catered to such wealthy young heiresses as Christina Onassis, girls who arrived each morning in chauffeur-driven cars. It was a school that at the time, according to one of Anna’s classmates, “prepared women to be educated wives.”

  Though Queens College had quite a lot of cachet and was very chichi, Anna despised it, hated putting up with the very intense discipline. Under the rules, students were not permitted to talk in certain parts of the building and were required to stand and stop speaking when a teacher entered the room. The school was kept so cold—warmth was considered bad for discipline—that a classmate developed a mild case of frostbite on her feet.

  Anna also hated the school uniform—a pinafore with a long-sleeved white shirt, striped tie, and cardigan sweater, which she thought was ugly and dated.

  With all of the discipline and regimentation, Anna was viewed as “willful, resentful, and very complex,” according to a classmate. “Anna didn’t seem to have a need for a lot of girlfriends. She didn’t have any really close friends, and if she did, she didn’t appear to keep any.”

  Susan Summers, who went to Queens and later worked for the Evening Standard, was once told, “When you meet Charles Wintour, you’ll be put off by his rather glacial exterior, but when you get to know him better you realize it’s only the tip of the iceberg.” She says, “There’s clearly a lot in common between Anna and her father in that they’re both cold. . . . The difference is, he was actually loved by his staff, and she was not a. popular leader. She had a pretty screwed-up childhood, and she became a very icy woman.”

  Anna remained at Queens College until July 1963, when the Wintours, tired of her complaints about how dreadful life was for her at the school, transferred her to another fancy all-girls’ school, the century-old North London Collegiate, where she was admitted on September 18, and where the students were known as “North London Clever Girls.”

  two

  A Teenage Bond

  At North London Collegiate, Anna bonded with another new student with whom she would have a seemingly loving and enduring friendship, albeit one marked by sporadic petty jealousy and Machiavellian cattiness. Anna’s relationship with Vivienne Lasky, her first and only true teenage soul mate, would eventually end years later, suddenly, sharply, and bizarrely, like a number of Anna’s subsequent adult female friendships and professional associations.

  Anna never was, and never would be, a girls’ girl, would have few close female friends over the years, and didn’t appear to like or enjoy the company of other women—curious for someone who one day would control fashion magazines that catered to women’s styles and taste.

  But back then, from the moment Anna and Lasky met in the dreary, frigid halls of North London Collegiate, about to turn fourteen, they became as close and dependent on each other as those four mop-heads called the Beatles who were about to launch the first British invasion of America. In the next decade, Anna would be among those at the forefront of a second—an encroachment upon the American shores of a brigade of British journalists, writers, and editors dubbed the “Briterati.”

  “We were the two new girls at North London,” says Lasky. “Being the new girls was not easy. No one else would talk to us. We felt very left out. Anna would ask me, ‘Do you know where we’re meant to go?’ We arrived totally unprepared and no one said, ‘Go here, go there.’ Nothing was made clear to us. It was not a warm and nurturing place. We used to have discussions, ‘How long are we going to be the new girls?’

  “I liked her immediately. I could see she was smart, pretty, didn’t seem stuck up. We were just drawn together and became best friends. Anna was half American, and I was half American. We were both living in Britain, and our fathers were in journalism. We fit easily into each other’s lives. We were as close friends as girls could be. It was just the two of us.”

  Like Charles Wintour, Vivienne Lasky’s father was a prominent journalist and editor. Melvin J. Lasky, a New Yorker, was cofounder and editor of Encounter, an influential intellectual monthly. During the 1950s and 1960s, the best and the brightest wrote for the journal: Bertrand Russell, Vladimir Nabokov, W. H. Auden, among other literary intelligentsia. Under Lasky, Encounter held what the British author and filmmaker Frances Stonor Saunders once called “a central position in postwar intellectual history. It could be as lively and bitchy as a literary cocktail party.” The magazine also became the center of a controversy when it was revealed that it received clandestine funding from the U.S. Central Intelligence Agency.

  There were other similarities between the two fathers. Like “Chilly Charlie,” Lasky had a reputation for being cold and tough. “Charles and my father, they were very critical,” Lasky states. “They edited in their own lives as well as in their work. If I said to Charles at Sunday lunch, ‘I’m reading a most marvelous book,’ he’d say, ‘What a bunch of slop!’”

  Wintour and Lasky both were womanizers, and the Laskys’ marriage was also troubled. Both Anna and Vivienne shared the emotional upheavals ignited by their parents’ travails.

  Lasky’s coeditor at Encounter was Sir Stephen Spender, the literary and art critic, journalist, and social commentator. Unlike Lasky, who had an eye for beautiful women, Spender was bisexual. His daughter, Lizzie Spender, had grown up with Vivienne Lasky and had attended North London Collegiate, where she got to know Anna. After a giddy and madcap life, the tall, elegant blonde, who was an actress and a friend of Prince Charles, settled down, and became the fourth wife of Barry Humphries, better known as the drag queen talk-show host and stage performer “Dame Edna Everage.”

  Despite all of those intrigues, none of it seemed daunting or of concern to Anna. As she told Lasky, “We’re the daughters of celebrities. So be it.”

  While the one subject at NLC that interested Anna was history, the most contemporary event taught was the Boer War, which Anna instantly dubbed “the Bore War.” Academic studies were of little interest to her. Anna loathed everything about school, especially the classroom couture. She thought the uniform “looked liked shit,” Lasky asserts. “It was the same color.”

  In fall and winter, young Anna, who one day would rule the fashion world draped in Chanel, standing confidently in Manolos, was required to wear a brown felt blazer that had the feel of a horse blanket, the jacket worn over a stiff, scratchy tan poplin blouse, and a pleated brown skirt that was too large because the elderly spinster educators who ran the school wanted her to grow into it. Anna complained that it made her look pregnant. Moreover, the skirt was made of a synthetic fabric that once actually melted when Anna leaned against a classroom radiator to try to warm herself. The powers at North London Collegiate, like those at Queens College, kept the heat in the bitter and damp midwinter at a minimum, thinking it would inspire the students to work harder.

  For a time, when she was at Queens, Anna had been a runner, the only extracurricular activity in which she is known to have participated during her school years. “When she was ten she was amazingly fleet of foot,” her father once observed. “Some sports instructor indicated that if she really worked at it she could probably become a sprinter of Olympic standard. That finished it. Anna said, ‘How frightful! What on earth will happen to my legs?’ and stopped running.”

  By the time she got to North London, the teachers had to force her to run. “She hated that,” Lasky recalls. “She’d hi
de in the toilet.” Manolo Blahnik was years away from designing Sex and the City shoes, but somehow adolescent Anna foresaw that one day her legs would be a part of her signature look, so they needed to be slender and shapely, not thick and muscled.

  Besides the impact she thought running would have on her legs, Anna avoided gym by either cutting the class or claiming she was ill because she was physically sickened by the suit she was required to wear—scratchy brown culottes with a culotte skirt studded with dozens of little buttons on each side that made getting in and out of the outfit a formidable task. All of this was set off by a light blue preppyish polo shirt, brown and blue being the school colors.

  Another reason she always tried to skip gym was that she had to participate in bare feet, a school rule based on some obscure turn-of-the-century health theory Anna feared picking up a skin irritation, such as the highly infectious virus called verrucae, a wart on the sole spread through athletic activity, which her friend had caught. “Actually, Anna thought it was terrific because I just got to sit on the bench,” Lasky recalls.

  But more, Anna feared that the barefooted gymnastics might disfigure her slender feet.

  Anna liked to show off her good legs and was at the forefront of the miniskirt revolution, the decade’s defining fashion statement then hitting London like a German V2 rocket during the Blitz.

  While the school skirt’s length was set by the headmistress and was meant to cover the crease behind the knee, Anna rebelled by wearing a belt to hitch up the waist or by rolling up the hem, which got her into hot water. A number of times Miss Dobson, the scary math teacher, caught her shortening her skirt.

  If “old Dobbie” caught Anna leaning out the window with her skirt rolled up and saw the back of her legs, she’d jab her hard with the chewed metal end of a pencil that once held the eraser and severely reprimand her. Other times, as Anna marched in line to morning prayers—the Church of England and Catholic girls prayed in the east gym, the Jewish girls in the west—she’d be spotted for shortening her skirt. The eagle-eyed teacher sneaked up behind Anna and pulled her sweater up over her head. Disoriented and frightened, Anna was yelled at and berated for breaking the rule. Anna was “scared shitless,” Lasky remembers, but believes she continually broke the rule in order to “get a rise out of them. The short skirt thing happened time and time again.”

  Anna’s stubborn decision to wear minis, to defy the rules, would eventually lead to serious problems at school.

  Most of the North London Collegiate teachers—all women—were unmarried, and some had lost husbands or fiancés in the First World War. Anna scoffed at them, whispered about them, joked that they were so doddering she was absolutely certain their men had been killed in the Boer War. Anna had already developed a thing about age and would later use it as both a creative tool and a weapon when she became a fashion editor.

  North London’s uniform changed slightly in the spring, when students were required to wear long gingham dresses in various shades of the ubiquitous brown. “It was like a Donna Reed dress hanging on Anna Wintour,” recalls Lasky, giggling at the vision of her defiant, fashion-forward friend looking like the wholesome character on the golden-age TV sitcom The Donna Reed Show.

  Outside of school, Anna was required to wear a brown beret and a knitted scarf that displayed the school colors. The beret was mandatory through all seasons, and North London girls wore it to and from school. However, at four o’clock, when classes ended, Anna and Lasky, on the way to the underground station, doffed their school covers and stuffed them into their book bags. Enough with uniforms! Enough with regimentation! All of which got Anna into more trouble on a number of occasions.

  Riding home on the subway one late afternoon, Anna and Lasky were spotted sans berets by a proud alumna and reported. “Some woman called the school,” Lasky recalls, “and said, ‘I’ve just seen two North Londoners not wearing their berets!’ We were the only two girls who lived downtown, so they knew it was us. We got caught a few times. We got called in to the headmistress’s office and Anna would just sort of bullshit them. ‘You mean I can’t take my hat off?’ she asked innocently.”

  A stern lecture, one of many she received during her school days, ensued. “Your uniform stands for something. It shows where you’re from,” the headmistress intoned. “You must always wear your beret proudly. You, Anna Win-tour, have to live up to your uniform!”

  With wrist slapped, Anna left, stifling a giggle. She didn’t care about the school’s dress rules. “It’s a stupid hat. I hate it!” And she continued not to wear it if she thought she could get away with it.

  Years later, after she became head of American Vogue, the beret was still on her “out” list. She called it that “awful brown beret” and suggested that the required school uniform might have been one of the reasons why she became interested in fashion in the first place.

  Not until she was swathed in Chanel and standing on stilettos at the helm of the world’s fashion bible would Anna fully live up to her uniform.

  Eating in public was another issue that school authorities seriously frowned upon. Unfortunately, Anna once again was a violator, caught gulping down an occasional biscuit, hungry for a quick sugar rush because she rarely ate at all. Each time she got caught, her parents were called. “What do you mean she was eating biscuits?” demanded a furious Charles Wintour of the headmistress. “I would think my daughter was hungry!” Arguing in Anna’s defense, he swiftly and pointedly ended the discussion. “What,” he asked, “is this idiocy?”

  At fourteen, stick-thin Anna watched her diet obsessively, mostly by not eating. Her school lunch usually consisted of a Granny Smith apple. Lasky’s mother, a former model, was worried about Anna’s health and thought she was too bony, though Anna felt she was fashionably emaciated like the premier model of the swinging sixties, Twiggy, whom Anna thought looked fab.

  “Anna only ate if it was something special,” says Lasky. “She always has had terrific self-control.”

  Anna was sickened even contemplating the school menu, which consisted of dishes such as “bubble and squeak,” so named because of the sounds that were emitted during cooking. It consisted of bland boiled potatoes and soggy green cabbage mashed together. Or a pudding with the saucy name “spotted dick,” which a British grocery chain wanted to change to “spotted richard,” because customers were too embarrassed to ask for it. At home, Nonie Wintour served a mousse called “housemaid’s knee,” which also disgusted Anna, who would bring leftovers to her friend, who ate it on the subway after school. Moreover, Anna didn’t feel that the atmosphere at school was conducive to a relaxed meal, what with one of the teachers seated primly at the end of the long table, carefully watching her deportment and manners.

  “The place was so stiff-necked,” Lasky asserts. “There was no warmth.”

  Only on special occasions did Anna gorge herself, such as when she and her friend cut into their formidable allowances and splurged on lunch at the posh four-star Caprice in Mayfair, which later became one of Princess Diana’s favorite Italian restaurants, or at the delectable Fortnum & Mason, just west of Piccadilly, for tea and a quick bite. Anna kept on top of restaurant, pub, and club ratings in trendy magazines and guides. “She always liked the best of everything,” Lasky says.

  Bored with school, Anna and Lasky played hooky, forging their parents’ signatures on official-sounding notes they typed, asking to be excused from classes because of an urgent doctor’s appointment or a great-aunt’s funeral.

  “We went to the ladies’ room in Trafalgar Square and changed into regular clothes. We’d go to museums. We’d go shopping. We’d go out to tea. We’d go to the movies. Anna loved the old romances, the black-and-white classics—Rebecca. We would walk miles to see them over and over again.”

  Ferris Bueller had nothing on Anna Wintour.

  three

  Swinging London

  Nineteen sixty-three, the year Anna matriculated at North London Colle-, giate, an explosion of
enormous proportions rocked Britain. It was dubbed a youth quake, a psychedelic nuclear blast of fashion, style, and music that quickly resounded around the world. And Anna came of age in that momentous time, infusing her with an extreme interest in fashion.

  “That moment in time that Anna and I were growing up in London,” Vivienne Lasky reminisces, “was just not to be replicated.”

  The hair—the sexy, sometimes fetishy but always timeless bob—became an integral part of the look in the swinging London scene. Always on top of trends, Anna rushed to get her lush, thick, straight brown hair cut and styled in the new fashion, which became a key component of her chic image, the cut she still wore in her mid-fifties, a cut that not so coincidentally has been favored and popularized by the British dominatrix, as Anna, the editrix, would later be described by some submissive and mistreated underlings.

  The bob had been around for ages, first given public attention in the 1920s when the actress Louise Brooks wore it as the character Lulu. Also a model, Brooks appeared occasionally in fashion ads exposing the bob to the masses, which helped define the flapper look. Now it would define trendy London birds in the revolutionary and exuberant sixties.

  Among those whose look inspired Anna to get the bob was Maureen Cleave, one of Charles Wintour’s talented favorites on the Evening Standardstaff.

  “Charles simply adored Maureen,” says journalist Valerie Grove, one of Cleave’s close friends and a colleague on the paper. “She was petite, dark, brisk, brilliant, clever, sharp, and very articulate—adorable in every way And Charles was absolutely enthralled with her. Maureen had the bob, and it became sort of her trademark. Everybody on the paper thought that Anna copied Maureen’s hairstyle and that is the origin of the Anna Wintour look. People thought Charles was expressing his adoration of Anna, and his ambitions for Anna, through his keenness for Maureen. It was really some kind of dynamic there.”