Among the people she impressed was Condé Nast's famed creative director Alexander Lieberman, who arranged for her to meet with Vogue editor Grace Mirabella. As Wintour recounted the story, Mirabella asked the young editor exactly what job she wanted at the magazine. Wintour smiled brightly and replied, "Yours."
The exchange proved prescient. Ordered to hire Wintour by Lieberman, Mirabella watched helplessly as her ambitious underling undermined her authority. "She'd go behind my back and redo layouts, bring in new art, circumvent me and my fashion editors," wrote Mirabella in her 1995 book, In and Out of Vogue. "When she couldn't bypass my editors, she'd harass and criticize them."
To stem the growing tension in the office, company chief S. I. Newhouse, smitten by Wintour's heady glamour, moved her first to British Vogue and then to House & Garden, which Wintour renamed HG and packed with so many celebrities the magazine was nicknamed Vanity Chair. The new look proved a disaster; circulation and ad pages plummeted and Newhouse had to set up a separate phone line just to handle calls from irate readers. But Wintour had impressed her boss with her stylish layouts and pop sensibility. In a way, she was applying for the job Newhouse eventually gave her in 1988.
"Vogue at the time felt too mired down in a very conservative look," says Si Newhouse. "We felt that Anna would bring a balance between high fashion and wearable, accessible fashion." In 1988, Mirabella was fired, and Anna was installed in her place.
Wintour quickly set about restoring Vogue's luster, turning it -- and herself -- into an unstoppable force in the $160 billion fashion industry. She locked up top photographers like Steven Meisel and Mario Testino with huge contracts and insisted on exclusives from top designers. She put New Society types on her masthead and ushered in a youthquake of new editors. In short, she gave the magazine a rarefied buzz that reestablished Vogue's position as a fashion arbiter.
André Leon Talley, Vogue's editor-at-large and Wintour's off-and-on confidant, who compares his boss to both Jacqueline Onassis and Catherine the Great, defines Wintour's winning formula. "She's very concerned that the kinds of fashion in the magazine address a real woman's needs as well as project a kind of attractiveness that will make people think Vogue is special."
"She's defined the modern powerful elegant woman," says Michael Kors. "Elegant women in the past were always sort of precious. Anna is all about the best of the future while holding onto some of the glamour of the past. She's the quintessential woman right now. Sleek, powerful, sexy -- that's what women want to be today."
Over the past decade, from her perch at Vogue, Wintour has not only dictated fashion tastes to the public but also influenced fashion's course in the back rooms of design shops as well. "She truly sees the magazine as a bridge between the designer and the consumer," says Donna Karan. Wintour is often called on by the world's biggest design houses to recommend new blood. She has single-handedly boosted the careers of favored designers such as Kors and Marc Jacobs, pushing their clothes to department stores and TV audiences. Another pet was John Galliano, whom she set up with a backer and virtually installed at Dior. "These are all behind-the-scenes things where we can help and we want to help," says Wintour. "Because it's all good for fashion." And it's good for business, too. "Whenever Anna gives us an editorial, we get a direct sales increase in the stores immediately," says Calvin Klein, another close friend of Wintour's. "It always happens."
Klein and other top designers return the favor by advertising heavily in Vogue. Wintour readily admits that if she has to choose between two equally impressive dresses, she will choose an advertiser over a non-advertiser every time. "Commercial is not a dirty word to me," she says.
Designers who fall out of Wintour's favor don't fare as well. When she stopped covering Geoffrey Beene in 1994, the designer stopped inviting her to his shows. "Wintour is a woman of simmering discontent," Beene said in a statement to New York, "a boss lady in four-wheel drive who ignores or abandons those who do not fuel her tank. As an editor, she has turned class into mass, taste into waste. Is she not a trend herself?"
If she is, the industry knows when to follow. When grunge failed to help advertisers sell beauty products and accessories a few years back, Wintour demanded an immediate return to glamour. "She went to the designers personally and told them, 'This is what we're shooting. If you don't do that, you're not going to be shot,' " says Times fashion editor Spindler. "And they all did it."
If fashion purists complain that Wintour has made Vogue too commercial, upstart lifestyle magazines like InStyle and Marie Claire, with their mix of celebrity editors and servicey fashion tips, are nipping at her Manolos from below. In just six years, InStyle has come from nowhere to claim a circulation of 1 million. In the same time period, Marie Claire has managed to attract a circulation of 700,000. W, Fairchild's large-format glossy, has jumped to 416,000.
Meanwhile, competition for ad dollars has sprung up on Internet sites, TV shows on CNN and MTV, and on newsstands, where 165 new women's titles have sprung up in the past ten years. "They've all nibbled away at Vogue and made the landscape a little more harsh," says Steve Cohn, editor of Media Industry Newsletter. "But it's always been No. 1 in terms of influence and ad pages."
At Harper's Bazaar, Kate Betts is reportedly planning to infuse the ultra-rarified magazine of her predecessor with a jarring dose of pop music and edgy culture news. She hopes to attract younger, hipper readers and halt the magazine's fifteen-year slide to fourth place in the core fashion books, behind Elle and W as well as Vogue. "Everybody is keeping an eye on her," says a rival editor. "But nobody is sitting there thinking Bazaar is going to be nose-to-nose with Vogue."
Still, Wintour and company are taking no chances. This spring, the magazine launched a massive publicity push, just to remind advertisers and readers who's on top. Nearly 2,000 city buses began carrying the slogan before it's in fashion, it's in vogue. The magazine has begun sponsoring concerts and street fairs. And it's aggressively pushing the upcoming "Millennium" issue, at 600-plus pages its biggest November issue ever.
Vogue's circulation of 1.1 million has dipped slightly since Wintour took over, dropping 100,000. But its ad revenues, though flat last year at $150 million, have perked up 9 percent already this year. Wintour and Newhouse say they're not worried about pretenders to the throne. "There's always going to be competition from one area or another," says Wintour. "I think one just has to remain focused on what you do. Maybe there's some bumps along the way. Some things are great. Some things are a disaster. But you just can't concern yourself with what everybody else is doing."
With the purchase of Fairchild, rumors have circulated that Wintour could be bumped upstairs to oversee a number of fashion titles -- with McCarthy eased in to run Vogue. It would make sense, since she just inked a reported five-year contract with Newhouse. "Like other middle-aged people who have achieved a lot, she sometimes says to herself, 'There has to be more,' " says one Wintour confidant. "This Fairchild thing, and a bunch of new Internet ventures, definitely give her some opportunity."
The Internet and its potential seem to genuinely delight Wintour, though she admits she still has trouble sending e-mail. When I mention Vogue's sleek new Internet site, she turns instantly animated, chatting excitedly about e-commerce and the site's picture quality. "I'm very excited about it," she says. "I want to do it right. I don't want to just rush in. I'm very interested in the commerce side, how it will support itself. The 'Index' section is something I've felt could work well in that area."
But despite the number of old-media bigfoots who have recently joined the Web gold rush, some staffers say high-tech glamour may not be enough for Wintour. Media reports and a few of Wintour's friends suggest she may covet the job of Condé Nast's shaggy young editorial director, James Truman. Truman and Wintour were once friends, but in recent years, sources say, the two have become increasingly distant. Wintour has made no secret of her disdain for Truman's performance at Condé Nast, and his impact on Vogue is minimal.
Is Anna gunning for his job? "I don't think so," says Truman, hesitantly. "She's never said or done anything to lead me to believe that she is." Newhouse is slightly more enigmatic. "I think Anna is capable of handling anything within magazine publishing," he says. We are sitting in his corner office, our knees practically touching, since he is hard of hearing and has pulled his chair close to mine. He is wearing black pants, loafers with raised white stitching, and a baggy pea-green sweatshirt. He vehemently denies that Wintour's travails have distracted her from her job. "Anna is driven by a desire to express herself as an editor," he says. "I don't think she thinks of herself as having a job anymore than Baryshnikov thinks of himself as having a job."
For her part, Wintour denies that she has career aspirations beyond Vogue. "I don't think I'd be any good at it," she says, downing her second cappuccino. "I just really don't. I don't have the sensibility to direct an editor of Bride's or Details or those other kinds of magazines. I think I can have opinions." She smiles slyly. "But I don't think they'd necessarily be right. I can't imagine anything better than Vogue."
Making sense of her home life is a more urgent question for Wintour. This month, Wintour began proceedings toward a divorce, but her friends say Shaffer is going to make it difficult. "I know she's totally distraught," says one, "because what she had with David was very deeply genuine, yet a very confused situation. But he certainly doesn't want it to end."
For Shelby Bryan, who is worth an estimated $30 million (including a $6 million home in Locust Valley and a $3 million home in East Hampton), getting out of his marriage will most likely cost half his fortune. He recently retained divorce attorney Robert Stephan Cohen, whose clients have included Christie Brinkley and Marla Trump. But his first move when the affair became public was to retain P.R. powerhouse John Scanlon. Mrs. Bryan is represented by Bernard Clair, whose last high-profile client was Jocelyne Wildenstein.
"I think Shelby's going to pay Katherine a lot of money," says a Wintour confidant, who claims that Wintour recently offered her former husband "a very generous settlement." If Wintour wants to keep her Sullivan Street brownstone, she will most likely need one of Newhouse's generous zero-percent mortgage loans, which he gives to senior editors -- perhaps as much as $1 million, a figure that's been floated in numerous gossip items. Neither Newhouse nor Wintour would discuss any such arrangement.
If Wintour and Newhouse have bigger plans for her future, they're not saying. And if Wintour is indeed on the edge of career burnout -- and casting her net a bit wider (perhaps hoping to become a "Washington hostess," as one friend put it) -- she's keeping it all to herself.
But to the outside world, it's clear that Wintour's once iron-maiden image has been irreparably smashed. Her allies say that's not such a bad thing. In fact, her hardships may prove to be strangely redemptive.
Patrick McCarthy, who was in Paris for the couture collections, accidentally ran into Wintour one evening at the Tuileries gardens, where Wintour had taken her children. "It was all glittery and lit up, and she was just having a ball, riding round and round with her daughter on this garish carnival ride. She was having a great old time. She even got me to get on."
Last week, as she prepared for Fashion Week, friends reported that Wintour had started to seem energized again, freed at last from the restrictive icon she had turned herself into.
"She's not hiding behind her glasses anymore," says a fellow editor and longtime friend. "Now she's having fun again. I look across the room and and see someone enjoying her life." To another observer, Wintour's long summer of discontent may turn out to be transforming. "She's never seemed so giggly and sparkly-eyed and beautiful and happy," says Mizrahi. "Listen, this doesn't look like a crisis to me. To me, it looks like a liberation!"