Friends also say that Shaffer played an important role in Wintour's ascent, spending hours on the phone with her every day, plotting her rise, taking care of the children, supporting her behind the scenes. "It was a very supportive, energetic, intellectual relationship," says one longtime friend. Wintour was proud of her husband's expertise in his field, and occasionally their worlds overlapped. When Donatella Versace's daughter, Allegra, began suffering from eating disorders, Shaffer stepped in and guided her treatment.
By the mid-nineties, however, their marriage had run out of steam. A man who vacationed with Wintour and Shaffer in St. Barths last winter recalls the couple's sitting next to each other on a beach for seven hours and never exchanging a word. "There was no sense that they were kindred spirits. They both just seemed incredibly sad and bored."
In contrast, Bryan was a flashy extrovert with undisguised social ambitions. A Wasp country-clubber with a notoriously roving eye, he was becoming a player both in Washington circles and on Manhattan's power scene. A friend says the pin-thin editrix gave him entrée into a more glamorous sphere. "It's all part of the turn-on," says a Democratic pol close to Bryan. "He loves all of this attention. The notoriety raises his profile."
Though Wintour has never lacked for a high profile, she was eager to broaden her circle as well. In recent years, she had become increasingly interested in politics. She peppered Vogue's pages with profiles of politicos like Madeleine Albright, Leah Rabin, and Katharine Graham. Last December, with the help of Oscar de la Renta, she scored a press coup, putting Hillary Clinton on the cover of Vogue soon after the president's Congressional impeachment. "The whole fashion kick was starting to seem a bit silly," says a friend. "Shelby was this real Type-A player kind of guy, and he gave her access to a whole different world."
In the weeks after they met, Bryan showered her with flowers and gifts. As the relationship progressed, Wintour's employees saw a noticeable transformation. Out went the dark glasses. In came highlighted hair and a decidedly un-Wintour-like glow. "It became pretty obvious," a Vogue staffer reports. "She started shutting her door whenever she got these phone calls." Another staff member says the cat was out of the bag when she began returning from long lunches with her usually meticulous hairdo noticeably askew.
Early one November morning, several months into the affair, a sharp-eyed acquaintance spotted Wintour and her alleged paramour exiting the elegant Parc Vendome apartments. Within hours, reports of the sighting were buzzing around the city. Ironically, Wintour may have been undone by her own fashion sense. The acquaintance had done a double take when she spotted a waifish woman draped in a chinchilla wrap, clearly meant for evening.
Bryan's wife, Katherine, had learned of the affair a few months before, and though she was devastated, friends say she was not exactly surprised. Three years earlier, Shelby had had an affair with another married woman. "Katherine worked hard to forgive him," says one pal. A refined Kansas beauty, Mrs. Bryan had given up her own career to push along her husband's. When she discovered his first affair, "Shelby was very apologetic. He said he had made a mistake and begged her to take him back." When another friend called a year ago and told her about Wintour, "she felt like she had been kicked in the stomach."
Mrs. Bryan wasn't the only one caught off guard. After finding a message Shelby left on an answering machine to his wife, David Shaffer phoned Katherine Bryan in a panic. "He was just like, 'Oh my God, your husband and my wife are fucking each other,' " says a lifelong friend of Katherine's. "He's supposed to be this brilliant shrink, so the whole thing was really weird. But he was obviously upset and disturbed by it all. He didn't want his marriage to end." Bryan listened sympathetically but told Shaffer she didn't feel comfortable discussing the matter. Soon after, she approached her husband and insisted that he end the affair.
Unnerved by the media attention, Shelby swore to his wife that it was over and presented her with a brand-new ring. He also agreed to buy a new Upper East Side townhouse. Katherine continued to painstakingly plan the elaborate wedding of Shelby's daughter, Ashley, which took place in June on the couple's sprawling twenty-acre Locust Valley estate.
The same month, Wintour and Shaffer presided over a celebration of their own: an engagement party for socialite Marina Rust that took place in their elegant Sullivan Street townhouse. As guests sipped wine in the dining room, Shaffer self-consciously toasted the couple, wishing them a lifetime of wedded bliss. Wintour, who one guest described as "insanely bubbly all night," did the same.
But their reunion turned out to be short-lived. By July, Bryan and Wintour began to see each other again. Bryan's wife Katherine, a trained marriage counselor, had agreed to salvage their union on the condition that they seek couples counseling. But "Shelby was very busy and kept putting it off, saying his schedule wouldn't permit it," says the longtime friend. "Frankly, he couldn't do it and keep living this dual life." Soon after, he moved out of their Upper East Side apartment and into Trump Tower. When news of their separation became official, says a source, Katherine received a surprise phone call from Air Force One. It was the president, calling to offer his condolences. As it turned out, Bryan's well-publicized affair nearly derailed his appointment to Clinton's prestigious advisory board on foreign intelligence. Anxious aides approached Bryan and suggested that he bow out until the affair blew over. Bryan refused.
Meanwhile, Wintour found herself putting out fires at work as well. Throughout her tenure, Wintour has governed Vogue with an unspoken set of rules. Food on the premises is discouraged. Junior staffers are not to speak unless spoken to. One young editor who made the mistake of greeting Wintour in an elevator was upbraided by one of Wintour's two personal assistants. Another, agonized over how to react when she saw the boss trip in a hallway, decided to walk past Wintour. When she told a senior editor what had happened, she was told "You did absolutely the right thing."
Wintour and her allies dismiss these reports as fantastic, saying Wintour's shyness is misinterpreted as haughtiness. But the effect seems to be visible when we meet at Wintour's office. As Wintour and I round a corner for the elevator, a young blonde in a tight black skirt and silk shirt waiting for the door looks panic stricken. She turns away before realizing there is nowhere to hide. As we wait silently, Wintour looks her up and down. The scene is repeated as two staffers joined us on different floors, until there are three young women solemnly standing in front of Wintour with their heads bowed like schoolgirls before a headmistress.
That's because in some ways Wintour is like a headmistress. Vogue has long been viewed as a finishing school for women from good families -- with enough of a trust fund to survive on low-paying junior salaries. Wintour's girls, as she calls them, are expected to be slim, pretty, and tastefully attired. She once told a reporter she wouldn't hire a fat person, even if she was a brilliant editor. She makes no apologies for it. "It's important to me that the people that are working here, particularly in the fashion department," she says, "will present themselves in a way that makes sense to the outside world that they work at Vogue."
Her own look carries a hefty price tag. In addition to a salary rumored to be close to $1 million year, she also receives lavish perks, including a $25,000 clothing allowance, a chauffeured car, Concorde travel to European shows, and a suite at the Ritz. Every Christmas, says one staff member, her accessories department "goes crazy" buying Wintour's presents for friends, family, and major advertisers. "Everybody feels really bad for the person who has to shop for Anna's family," says the staffer.
Among those who flourished in this high-strung atmosphere was Kate Betts, who started off at the magazine as a fashion writer and soon became Wintour's protégée and presumed successor.
Headstrong and famously opinionated, Betts had come up through the fashion press under the tutelage of John Fairchild, the famously grumpy founder of Fairchild Publications. At Vogue, where she landed eight years ago, her brassy confidence was an asset. "Anna liked Kate," says one editor, "because she had the balls to argue with her." Wintour doesn't disagree. "I do like Kate," she trills at lunch. "She had a point of view. She was strong and not a mouse. What's the point of sitting there with a bunch of mice? I'd have no fun!"
Betts helped improve Vogue's news coverage, broadening the magazine's reach into general culture and writing gritty stories on street culture, women in politics, and the financial travails of top designers. In 1995 she conceived and edited the popular "Index" section, a trendy but servicey compendium of beauty, style, and shopping tips. "Kate felt you should be able to tear out pages and have information you really need," says arts editor Michael Boodro. "She wanted the look of the moment: who's designing it and where you can buy it."
But Vogue insiders say that Betts's relationship with Wintour withered over the past year as the two disagreed over story ideas. Betts felt that Vogue's fashion coverage had begun to look narrow and stuffy. An astute observer of pop culture, she assigned stories on music, street fashion, teen tribes, cyber culture, and television. "Anna had a different idea of who the Vogue reader was," says a Vogue source. "She felt stories like these were beneath them."
The office atmosphere further deteriorated when Wintour began pitting Betts against a more recent favorite, 29-year-old British socialite Plum Sykes. Though Wintour was impressed by Sykes's glossy pedigree, Betts, says a friend, dismissed the young editor as "a pretentious airhead." The two clashed frequently. "Kate despised Plum," says another source, "but Anna enjoyed making them work together. I think it was her way of keeping Kate in line."