Front Row

by Jerry Oppenheimer

  It was, as Grove notes, “an appropriate house for an editor of a newspaper in those days, and for an American heiress. The first thing anyone said about Nonie when one first arrived [on staff] at the Evening Standard was ‘Charles Wintour has a rich American wife.’ It was understood that, however well-heeled his army family was, it was Nonie’s money that had enabled them to buy the house in Kensington.”

  Alex Walker believes that Beaverbrook may also have had a role in helping Wintour with the purchase, by giving him a loan, the kind of special perk he offered favored high-level employees. (Years later, Anna would also have a powerful and enamored media king for a boss, Condé Nast’s S.I. Newhouse Jr., who is said to have assisted her, too—one of his favorite editors—in buying a town house in Greenwich Village with an interest-free $1.64 million mortgage on the property from Condé Nast.)

  Back then, though, teenage Anna didn’t care how her parents got their financing. She adored the fact that they now lived in a classier neighborhood, closer to the action, with powerful and well-to-do neighbors, and fancy shopping steps away. But most of all, she was enthralled with the lower level of the house, where there were servants’ quarters—a staff flat, consisting of a living room, kitchen, and bath, with a private entrance.

  Anna believed she was old enough to have her own place, even though it was just a stairway away from the rest of the family. She asked, and her parents readily agreed. The permissive Wintours viewed Anna as mature and responsible enough to live somewhat independently from the rest of the family and felt that she deserved her privacy They were ahead of their time—by the nineties homes would be built with separate teenager suites.

  “So, at fifteen, Anna had her very own flat and total privacy to come and go as she wished,” says Vivienne Lasky. “Once she had her flat, she didn’t really participate upstairs at her house unless it was Sunday lunch, which was sort of sacrosanct in the Wintour household. She was very precocious, very adult, and was playing at being an adult.”

  Discerning and opinionated about what she wanted, Anna furnished most of her flat at Habitat, the decor lifestyle store that brought designer Sir Terence Conran to prominence, a store that sparked a design revolution in the middle-class British home. To Anna, the shop was known as “Shabitat” because everything was relatively inexpensive—her parents footed the decorating costs, of course—but had a chic look. Habitat was the Ikea of its day, only classier.

  Anna’s bedroom was all blue and white, but spare, and not very girly-girl. Against one wall was a fabric-covered kidney-shaped dressing table. The duvet on the queen-sized bed had matching fabric. (Conran asserted later that his introduction of the duvet had a positive impact on the supposedly boring British sex life because the cover made it so easy to make the bed and hide the evidence after a quick romp, and it also had a sexy, Swedish overtone.) Anna’s living room had floor-to-ceiling shelves, a wall filled with her parents’ books—she enjoyed Doris Lessing and Agatha Christie. In the bathroom she had a large framed purple poster promoting a New Year’s Eve party she had attended at a hotel discotheque in Zurmatt, Switzerland, during a ten-day Christmas vacation with Lasky and Anna’s younger brother, Patrick. The flat opened through French doors onto the pretty landscaped garden that included a little pond with a water-spouting frog. The garden backed on to the greenery and flowers of Holland Park. It was a suite fit for a princess.

  But, surprisingly, the parents of the woman who one day would be noted for her sense of style and be appointed editor of the venerable House & Garden magazine had little if any taste of their own.

  Aside from Anna’s room, the rest of the enormous Wintour house was, observers maintain, horribly decorated in a glitzy contemporary American style. “Charles had very little visual sense of his surroundings,” notes Valerie Grove. “He was a cerebral person but was not into decorating a house in an appropriate style. I don’t think he particularly minded what backdrop he had as long as it was neat and tidy and businesslike. I never ever thought of Charles and Nonie as having a cozy or comfortable or warmly welcoming atmosphere.”

  By her midteens, having her own flat and lots of independence, the world of dating and night-clubbing opened up for Anna.

  Swinging sixties London was at her pretty feet, and men, young and old alike, were mesmerized by her appealing face, her ivory skin, her chic shiny bob that gave her an exotic with-it look, those skinny legs in the shortest of minis, and a Lolita-like come-hither shyness—an enigmatic quality that excited men all the more. All in all, Anna Wintour at fifteen was an alluring package and quite a catch. Another component of her aura was her father, a powerful figure in journalism and a lure for some of the up-and-coming scribes who pursued her. And Anna was immensely attracted to writers and journalists, and the older, the better. Over the years she would be drawn to father-figure types, surrogates, in a sense, for the absentee Charles Wintour, whose primary family was his newspaper.

  As one armchair psychologist who worked on Fleet Street in those days, and who squired Anna briefly, notes, “I always felt she was chasing the daddy figure who was never around. She was like a needy, shy little girl, and I think that was all a bit of an act to get your full and undivided attention, which she never got from old Charles.”

  The first in a relatively long queue of older men whom Anna dated was the future best-selling and critically acclaimed author Piers Paul Read, who at twenty-four was a year or two out of St. John’s College, Cambridge, where he had studied history. Fifteen-year-old Anna met Read, aptly enough, at a wedding—the nuptials of her first cousin on her father’s side, Oliver James, a future professor of geriatric medicine, and Roseanna Foster, one of Read’s closest childhood friends from his hometown of Yorkshire.

  Among the conservative guests at the wedding party, Anna stood out, a chic and seductive vision to Read, who was instantly smitten with this sensual teen in a pink miniskirt and heels, flirtatiously hiding behind the long bangs of her bob, giving her an air of mystery.

  “Here was Anna, this sexy and pretty teenager, at fifteen, and I was this depraved twenty-four-year-old,” says Read, half jokingly “She was very young, very pretty, very sophisticated, very sort of culturally up-to-date, and just slightly timid.”

  Though to Read she exuded extreme poise and confidence, model-thin Anna was unnecessarily consumed with, and obsessed about, her weight and didn’t think she was attractive, despite the way she lorded the poundage issue over Vivienne Lasky. “She hated the photographs that were taken of her at Oliver’s wedding,” recalls Lasky. “When she saw those pictures, she said, ‘God, do I look terrible.’ She thought she was chubby. She thought her legs looked awful. She thought she was not photogenic. She looked at the wedding pictures and said, ‘Good God! Is that how people see me?’ I said, ‘You look fine.’ She said, ‘But just look at my knees! They’re ugly.’ I mean, she was just a kid, but she was so involved with how she looked. She said, ‘Your knees don’t look like mine. Mine look bigger,’ and she actually took out a ruler and measured her knees, and then measured my knees. Her knee bone was wider than mine. She was so upset.”

  Anna was a firm believer in Mary Quant’s adage that “a woman is as young as her knees.”

  The width of Anna’s knees notwithstanding, Read was hooked and so was Anna, though each had his or her own agenda. He appealed to her elitist tastes, was an intellectual of sorts, and already was being talked about as having a great future as a writer; therefore, she was fired up to go out with him, a trophy kind of guy, plus—and this was a big plus—he was older. Her interest in men of letters, as it were, was passed on to her by her father, who thrived on the excitement generated by being among journalists, of discovering new writing and editing talent, especially of gaining access to and being among celebrities, a taste Wintour had inherited from Beaverbrook and that he handed down to Anna, a taste she would cultivate throughout her life.

  “Piers was very talented, very British,” observes Lasky. “He was older, sort of funny-looking
. But his smile was devastating. For Anna, it wasn’t so much a man’s looks as [his] brain.”

  Read was commuting between Yorkshire and London and working on his first novel when he and Anna began dating—inexpensive dinners, the cinema, visits with the Wintours. He couldn’t afford much more, which wasn’t the way to win Anna’s heart. “If you were to take Anna out on a date,” recounts Lasky, “she expected it to be as fancy and well planned as any she would arrange for herself She had very high expectations.”

  Nevertheless, Anna had a major crush on Read, which wasn’t quite reciprocated. Aside from her sexiness, Read states, “Anna wasn’t particularly interesting. She was a curiosity as much as a sexual desire.”

  But through Anna, the ambitious Read hoped for access to a higher stratum of society, which was his main agenda. “I felt that I could sort of get to know London and the influential people in the big city,” he acknowledges, “by sort of chatting up the daughters, as it were.”

  It was an eye-opening experience for this young man from the north of England who had never known a girl quite like Anna, especially such a young one, who had her own flat, free to come and go as she liked and to entertain friends there. Read also was surprised that the Wintours didn’t mind that Anna was dating a man nine years her senior, though he was certainly respectable.

  “I was and am a Roman Catholic, so their kind of liberal take on things wasn’t quite mine,” he notes. “They had different values. They were fairly antireligious. And Anna’s parents had a very sort of liberal attitude towards sex. I was sort of horrified and fascinated at the same time by their sexual permissiveness. I’d been brought up with sort of rather straight, Catholic views. When I visited Phillimore Gardens it was with a combination of fascination and horror. I don’t want to give the impression that I was priggish or disapproving, but I was a Catholic country boy from Yorkshire, sort of an incredibly muddled young man at the time, and I had the feeling I was in Sodom and Gomorrah. But you know, it was the sexual revolution, so I didn’t mind cashing in on that.”

  But he says he didn’t get past third base.

  “Nothing irrevocable happened between us,” he claims. “I was quite young and inexperienced. We held hands, kissed occasionally. I don’t know for certain, but I don’t think Anna had lost her virginity when I went out with her. She certainly didn’t give me the impression that she’d been to bed with anyone, but I could be wrong.”

  To Anna’s shock, horror, and dismay, Read suddenly and with finality ended the relationship—stopped seeing her, stopped calling her, disappeared off the scope, as it were, after telling her he didn’t think their relationship had much of a future.

  As Lasky recalls, “Anna was more keen on him than he was on her. But she wasn’t ready to give him up.”

  Anna had difficulty dealing with the young writer’s rejection and did not take kindly to having someone else decide what course her life would take. More appalled than confused that she’d been the one to get the heave-ho, Anna demanded answers. But rather than confront Read herself, Anna enlisted her best friend as her intermediary.

  Anna told Lasky she didn’t want to meet with Read because “she was afraid she might become clingy” and believed her friend could be more objective in confronting him.

  Anna Wintour clingy?

  Indeed, Anna’s handling of the matter underscored a growing neediness involving men that would become even more apparent in later years—a shocker to female colleagues who viewed her as a strong and independent ice queen.

  “Clearly, Anna didn’t believe Piers’s explanation, which was that Anna was too young for him. She said to me, ‘I want you to call up Piers and see if you can meet him for lunch.’ She wanted me to ask him basically why he dumped her,” Lasky says. “Piers was very British, and I guess he hadn’t made it terribly clear. So I was meant to plead Anna’s case, to find out what the hell was going on, because Anna didn’t want the relationship over. She was my best friend, so I agreed to do it. I had to schlep way across town.

  “I said to Piers, ‘She’s not really quite clear on what’s going on. She doesn’t want to lose your friendship. Anna feels the story is unfinished’—all that sort of crap you say. I said, ‘She’s my best friend. I’m here for her. She doesn’t quite understand the situation. Talking to me is easier than talking to her because there aren’t those feelings.’

  “And he just said, ‘I’m much older than she is. I don’t think the relationship is going anywhere. I don’t have those feelings. She’s too young.’”

  Read also indicated that there might be someone else in the wings.

  Back in her flat, Anna anxiously awaited Lasky’s report. “The first thing she asked me was, ‘Well, did you plead my case?’ I told her it was a nice lunch, not very awkward, and I guess he realized he hadn’t handled it very well with her. I told her what he said, and I said, ‘I don’t think you have a chance with him.’ I was honest. I said, ‘It’s clear, whatever it is, he does not want to pursue it with you. It’s not like there was a misunderstanding, or you did anything wrong, or disappointed him. It just wasn’t to be.’ She said, ‘Well, did you really try hard enough? Did you really put my case forward? Because I think he won you over. He didwin you over.’ She didn’t show anger or emotion—that’s not Anna. But the later Anna, the Anna of today, would have held it against me that I hadn’t completed the task and gotten him back for her.”

  As it turned out, there was another girl who had captured Read’s interest, and she was just a year older than Anna; his future wife, sixteen-year-old Emily, a student at the French Elysée in London.

  Over the years, Anna and Read would continue to have contact: Emily Read became a contributor to Vogue, and one of the Reads’ children became an executive in London for Condé Nast.

  Anna’s enduring friendship with Read is not an anomaly. Many of the men she was involved with over the years have remained loyal to her, even ones on whom she cheated.

  Around the time the romance with Read ended, Anna dated the only young man known to have been in her age group, a quintessential good-looking British preppy from a good family—well brought up—who took her to the races at Ascot.

  five

  London Party Girl

  More in line with the kind of men Anna was drawn to was a hustling, ambitious charmer of a Fleet Street “hack” named Nigel Dempster, almost a decade her senior. When Dempster began seeing sixteen-year-old Anna, he was digging up dirt at parties for London’s Daily Express gossip column.

  Anna was attracted to Dempster’s good looks and debonair manner, and especially his growing circle of fancy friends and the posh riffraff he attracted. Vivienne Lasky, however, came away feeling he was “smarmy and slimy.” And Charles Wintour’s blood boiled when he discovered that his daughter was seeing “a gossip hack.” For the most part, Anna’s father was rather sanguine about the men she dated; Dempster was a glaring exception.

  There were other facets about Dempster that were appealing to Anna, such as his purported lineage: He claimed he was a member of one of the two families who founded the powerful Elder Dempster Lines, a shipping company that controlled West African trade beginning in the late nineteenth century and were on a par with the Cunards. There was even a glossy in circulation of Dempster at the age of twenty in white tie and tails, which he asserted was a family society shot.

  Whatever the truth, Anna was intrigued, and Dempster, always on the make, saw both journalistic and romantic possibilities with her. The two became an item. They had much in common, sharing similar interests and values: power, wealth, and celebrity. Journalist Paul Callan, who would later have his innings with Dempster, notes, “A lot of guys wanted to go out with Anna because they wanted to curry favor with Charles Wintour—and that included Dempster.”

  Through Anna, Dempster had fantasies of becoming Charles Wintour’s big gun: His goal was to be the best-known, highest-paid gossip columnist of his time. The latter would come to be, but without the help of Anna�
��s father, who thought he was a cretin.

  Years later, Lasky still couldn’t see what Anna saw in Dempster. “He was so quintessentially British, backstabbing, and bitchy,” she says. “I didn’t think he had a moral fiber in his body . . . charming to your face, then ‘that slut.’”

  Through Dempster, who was beginning to hobnob with the highbrow and lowlife of British society and celebrityhood, Anna became a fixture of sorts on the London party and club circuit, not quite the Anglo version of a Hilton sister but considered hot stuff and recognizable to the cognoscenti (Fleet Street reporters who also made the scene and who knew who her father was).

  Friday evening before going out, Anna watched Ready, Steady, Go! And first thing Saturday morning she was at either Biba or Mary Quant, two of the hippest boutiques, shopping for the kind of kicky, sexy outfit Cathy McGowan had worn on the tube the night before. Saturday nights, she trucked off to the Laskys’ palatial duplex apartment overlooking Hyde Park for dinner, with eight o’clock set aside to watch The Forsyte Saga.

  At eleven—never, ever earlier because it wasn’t fashionable—she’d trot off to the clubs, usually starting her rounds at midnight at Dempster’s main hangout, Annabel’s, filled with an assortment of aristocrats, real and self-styled, and a slightly louche gambling crowd. Anna loved the attention of the men, consumed the bitchy gossip, and kept a sharp eye on the women—what they were wearing, how they wore it, what was in and what was out.