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The November Issue

The political philosophy of Anna Wintour.

Earlier this year, Anna Wintour visited Obama headquarters in Chicago to talk numbers with the campaign’s top fund-raising brass. As she headed into her meeting, Wintour passed a tray stacked with food for volunteers: glazed doughnuts festooned with bacon, classic campaign fare. “I trust you’re not interested in that,” a staffer jokingly offered. She fixed him with her cool, disdaining stare.

There will always be certain, crucial differences between politics and high fashion—“wedge” shoes or issues? Thomas Nast or Condé?—but, after raising more than a half-million dollars this election cycle alone, there is no doubt that Wintour belongs in the inner sanctum of the campaign, whatever her opinion of the menu there might be.

Though the campaign declined to break out Wintour’s exact fund-raising total, the past year has seen the editor become one of President Obama’s top bundlers—in addition to that $500,000, she has co-hosted four dinners at more than $30,000 a plate and has been heavily involved in merchandizing efforts, prevailing on friends like Marc Jacobs and Thakoon Panichgul to design Obama-branded merch. (The designers teamed up on Bark for Obama pet accessories.) In a season that’s increasingly seen banker money go to the other guy, Wintour’s connections and influence in Hollywood, fashion, and society aren’t merely pretty, shiny things to have around; they’ve become vital to the financial success of the campaign.

Wintour’s very public work on behalf of the Obamas might tell us as much about them as it does about her. From the beginning of their national political career, the couple appeared eager to be associated with Vogue. The campaign—or at least Michelle Obama and staffers like Desirée Rogers—understood that image is the coin of the realm on the stump as much as it is at Condé Nast. Rather than condescending to Wintour, they took her seriously to begin with, and so she began to work seriously for them.

It’s hardly that Wintour hasn’t thought about politics; she’s always cared about world affairs—or cared about looking like she cares. Her father, the esteemed editor of the London Evening Standard, once recalled a story of how a young Anna spent two hours deciding what to wear to an anti–Vietnam war protest. (“Daddy, am I for or against Cambodia?” she asked.) In those days, Wintour palled around with the likes of Christopher Hitchens and Martin Amis; and she dated a string of countercultural men, including the underground journalist Richard Neville. (There was also a rumored tryst with Bob Marley.)

But it was Wintour’s sister, a labor activist, who followed in their social-worker mother’s humanitarian footsteps. (Brother Patrick grew up to become the political editor of The Guardian.) Wintour was more of a dilettante—drawn to the left, but the more glamorous parts, and with little specificity about what, precisely, being on the left meant, other than knowing that it was where the cultural heat was. Today, she still has a lingering sense of insecurity about her intellectual chops. “I think they’re very amused by what I do,” she said of her family in The September Issue, a 2009 documentary about the magazine.

When Wintour ascended to the top of American Vogue, she took pride in introducing political coverage to the fashion magazine’s pages. She was a Hillary Clinton fangirl from the start, publicly offering the first lady pro bono fashion advice and reportedly goading designer Donna Karan into sending one of her famous cold-shoulder dresses to the White House. In the wake of the Monica Lewinsky scandal, Vogue published a profile that was important in shaping the public image of Hillary as a dignified, elegant survivor; a similarly glowing story followed when she ran for Senate.

So when, in 2008, Clinton declined to appear in Vogue, it was a snub Wintour took personally. In a blistering editor’s letter, Wintour suggested that the then–presidential candidate was afraid of looking “too feminine.” “The notion that a contemporary woman must look mannish in order to be taken seriously as a seeker of power is frankly dismaying. ... Political campaigns that do not recognize this are making a serious misjudgment.” She followed it up with some specific, passive-aggressive hints for the former first lady. “[W]e would love to see her wear a demure coat in delicious purple by Carolina Herrera to memorial services on Martin Luther King Jr. Day.”

The Obamas never made the mistake of underestimating Wintour’s capital and reach. Michelle was profiled in the magazine in 2007, at the very beginning of the couple’s fame—and the same year that Wintour began working on their behalf. (She raised $200,000 for the campaign in 2008.) Later, when they’d won the White House, the first lady sat for a cover, and Vogue was given the kind of access most Beltway insiders would kill for.

JOURNALISTS AND POLITICOS have tried to guess what Wintour could possibly hope to get from the campaign. The Guardian, her brother’s employer, cheekily suggested that she’s after an ambassadorship. But her minions dispute any conventional ideological motive. “Above and beyond any politics, she wants Vogue to be wherever the action is,” says a former staffer. In other words, she’s in search of something more than just a victory in November; she wants politics to take fashion seriously. Over the past half-decade or so, as her own profile has risen, so too has Vogue’s political coverage. It’s no longer just the occasional first-lady portrait session; now, there’ll be a promising governor (Sarah Palin, pre-John McCain), a stylish staffer (Huma Abedin), a first-time senator (Kirsten Gillibrand, soon after a dramatic weight loss), or a crusading bureaucrat (Elizabeth Warren). (Though it’s worth noting that Republicans have recently been less eager to appear in the magazine. A hoped-for profile of Ann Romney fell through earlier this year, says one person with knowledge of the negotiations.)

The hallmark of these pieces, naturally, isn’t their take on FinReg or Medicare but rather how their subjects handle and seek power, and what role fashion plays in their stateswoman-chic lifestyle. Do they accord it—and, in turn, the editor of the industry’s signature magazine—the importance it deserves? Vogue appears to take particular pleasure in publishing quotes that repudiate Clinton’s political-feminine divide. “I am not against spending money on clothes,” Elizabeth Warren, consumer defender, was quoted as saying. “As long as you are straight on your fixed expenses [housing, food, utilities, et cetera] and you have put aside 20 percent in savings, go ahead and buy those $400 shoes.” International Monetary Fund chief Christine Lagarde is described as “natural, open, and perfectly feminine.” “I am going to recommend this to your readers,” Kirsten Gillibrand said. “I had saved all my 4s and 6s from before I had children, but when I started this diet I said, ‘I’m going to give away all my clothes because I want to start fresh’ and I wanted to reward myself; if I ever get back to that size, I can buy new clothes.”

This approach is not without its problems, however. Consider the matter of Vogue’s glowing profile of Syria’s Asma Al Assad, which described the dictator’s wife as “glamorous, young, and very chic—the freshest and most magnetic of first ladies,” and breezed by her husband’s brutal reign by explaining that he was elected president “with a startling 97 percent of the vote.” “They didn’t think the Arab Spring was going anywhere, and the piece was needed for the March ‘Power Issue,’” wrote reporter Joan Juliet Buck in her Newsweek apologia. Wintour has also issued an apology. But perhaps she ought to have inquired earlier: Are we for or against Syria?

Despite the occasional misstep, Wintour’s influence continues to multiply. This month, the magazine scored a rare, all-access interview with Chelsea Clinton in which Hillary herself makes a cameo, devouring interior design magazines and bugging her daughter for grandchildren already. Too unserious for someone who might be considering another presidential run? Not in the Anna Wintour era.

This article appeared in the September 13, 2012 issue of the magazine.