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“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
didw
in 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.

M
ore 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.

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.

I
f 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, Griggs 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.

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.

“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.”