The Final Boss

So many media bosses dress the same—Veilance windbreakers or Patagonia fleece vests, leather Lanvin or Nike Flyknit sneakers, Brunello Cucinelli T-shirts with Levi’s 514s—the uniformity of their wardrobes in stark sartorial contrast to the volatility of the journalism business. But then there is Anna Wintour—who, for more than thirty years, has been the editor in chief of Vogue, a fixture and a force in the fashion industry who has also risen through the C-suite of Condé Nast. In her current role—as worldwide chief content officer, a title invented for her and one of unprecedented power in the history of magazine publishing—she oversees the editorial work of every Condé Nast publication domestically and internationally. Elements of her appearance have become such trademarks that they are inseparable from her mythology: the blunt golden-brown bob that is professionally blow-dried every morning, reportedly at Condé’s expense; the possibly-prescription sunglasses she wears everywhere, even and especially indoors; Oscar de la Renta and Carolina Herrera dresses; high heels that don’t bother her, thanks to the chauffeured car that was a condition of her employment. Over a long career, she has clung to an image of herself, and adapted it. She knows that she is being looked at, and she controls how she is seen.

In May, Amy Odell published Anna: The Biography, a 447-page book with a level of reporting, research, and analysis that makes it as close to definitive as an “unauthorized” biography can be. Wintour is famously reticent with her participation in such projects; the significant last biography on her—published in 1996, by Jerry Oppenheimer—is the reason so much gossip about Wintour’s life still circulates; it was absolutely unauthorized. Odell’s book, neither ignored nor approved, could be considered “semiauthorized,” if such a category existed. She made a few requests for Wintour’s participation; after Odell told a representative that her goal was to write about “a woman in a unique position of power,” Wintour provided a list of close friends and colleagues, with, it seems, an implicit understanding that those people had been given permission to speak—the “AWOK,” as her breezy sign-off goes.

Odell—a longtime blogger for The Cut; the former Web editor of Cosmopolitan; and the author of a collection of essays, Tales from the Back Row: An Outsider’s View from Inside the Fashion Industry—was approached by her publisher about this project in 2018. That year, there had been a credible rumor that Wintour might step down: her daughter Bee Shaffer was about to marry the son of her longtime friend and colleague Franca Sozzani, who had died of cancer two years before, and Page Six was reporting that Wintour might want to retire. “I felt like the opportunity was to ask how she became powerful, what makes her powerful, and how she has held on to her power for so long,” Odell told me. “I remember an early conversation with one of the editors I worked with on this. She said it’s the idea that’s hiding in plain sight.”

The resulting book has a balance of nostalgia (remember when editors had influence?) and contemporary context. There is the importance of her father, Charles Wintour, one of the most well-respected newspaper editors of his time. As Odell writes, he “proved that a tabloid could be both populist and sophisticated.” Vogue’s editorial mandate is notably similar: celebrities on the front, politically and culturally relevant coverage inside. There is also the tragedy of Wintour’s family: the death of her older brother when he was only ten years old, her mother’s subsequent struggles with depression and anxiety. There is Wintour’s time as a teenager in London during the sixties, when her father’s status came in handy getting a job at Biba, the hottest place for miniskirts (she was allegedly fired, like most of the other shopgirls, for stealing). Despite the tantalizing rumors that have circulated for decades, there is no basis to the story that Wintour had an affair with Bob Marley. She did date Christopher Hitchens, though, and was apparently “mad” about him. Wintour cried more than I would have expected over the course of her career, including when her colleagues at New York magazine noticed that she put her hair up in little ponytails with rubber bands and started copying her, which she found cruel. In 1981, Wintour spoke with Grace Mirabella, then the editor of Vogue, and was asked what her dream job was. “Yours,” Wintour replied. She was hired as a “creative director” for her first role at Vogue—a title, much like the one she occupies now, invented just for her. She ran track in high school and once, when she was mugged in New York, chased and caught the thief—in heels. She hates vegetables.

Already, coverage around the release of Odell’s book has delighted in these details. Of course, there was never a shortage of sources with Wintour stories to tell. But there had been a shortage of people willing to speak without her approval. As R.J. Cutler, who directed a documentary about Vogue called The September Issue, once told a friend: “You can make a film in Hollywood without Steven Spielberg’s blessing, and you can publish software in Silicon Valley without Bill Gates’s blessing. But it’s pretty clear to me that you can’t succeed in the fashion industry without Anna Wintour’s blessing.” In the acknowledgments section, Odell thanks Wintour.

 

Wintour occupies an unusual position between cult figure and full-blown famous person. She is recognizable enough that, in the right context (including the title of Odell’s book), calling her “Anna” suffices. For all the many obituaries that have been written to the star editor, she is the rare one who has survived and thrived, ascending as a business leader at Condé Nast and in the fashion industry. By a few measures, she may be considered the “final” boss. Yet as her influence has grown, so has the imperative for substantial critique and for reckoning with what her power means.

A throwback: In 2006, when Dodai Stewart applied for what would turn out to be a founding-editor position at Jezebel, she submitted an email with the subject line: “Writer and Magazine Junkie Seeks Full-Time Job, Love from Anna Wintour.” Recently, Stewart dug it up from her archives and read it to me. “I wrote that, as a Black woman who adores fashion, I feel personally slighted by every issue. But I go on to say: ‘Do I stop reading Vogue? No.’” At the time, there were a handful of websites posting faithful critiques, a few dedicated writers on the fashion industry. Odell began her career at New York and once interviewed for a staff position at Vogue (“So you’re one of the people who stalks me on The Cut,” Wintour said). But as Stewart told me, it was still slightly controversial to talk about diversity and inclusion. “It used to be like, Well, if you don’t like it, don’t read it,” she said. “There was less of a welcoming atmosphere for that conversation, and now everybody is having that conversation.”

Wintour’s public displays of overt racism and bigotry have long been documented, as in the case of the 2008 LeBron James and Gisele Bündchen cover, which resembled a King Kong poster (Odell reports that multiple staffers tried to warn Wintour against publishing it). Odell’s book has more examples: At a meeting in 1994, Wintour said she “wanted to do something about Asians. They’re everywhere.” She pressured Oprah Winfrey to lose twenty pounds before she put her on the cover. When a senior editor took a day off for Yom Kippur, Wintour asked if she was “off being Jewish.” When Men’s Vogue was still being published, she often expressed concern that it was “too gay”; sometimes Wintour would note that there were “enough” lesbians in an issue. In his memoir The Chiffon Trenches, André Leon Talley detailed how he felt disrespected and discarded by Wintour after a long career with Vogue. He’d sent her frequent memos appealing for more diversity in the magazine, about which she supposedly said to another editor: “Could somebody please tell André that not every month is Black History Month?” Edmund Lee, a New York Times reporter, told me, “Given her vast influence over fashion, the whiteness of fashion in many ways reflected her power.”

By 2020, during the summer protests for Black lives, when companies put out statement after statement pledging their commitment to address racism, classism, and misogyny, Wintour sent an email to her staff apologizing for not doing more to make Vogue inclusive as a magazine and a workplace. In the following days and months, the Times published two articles addressing Wintour’s profound mistakes—“Can Anna Wintour Survive the Social Justice Movement?” and “The White Issue: Has Anna Wintour’s Diversity Push Come Too Late?”—that together suggested a call for her resignation. Lee wrote the latter, for which he and his editors granted his sources full anonymity, recognizing the threat of retribution. “The retribution surfaces in the icing-out,” he explained. In media, diversity is often relegated to hiring practices, in lieu of addressing systemic inequities; Lee found there were only so many people who could speak to their experiences, and it would be immediately obvious to management who they were. “You could, in effect, disappear from the world of fashion”—a highly specific beat, in journalism, and a ferociously competitive business. “I credit my sources for taking a chance with us,” he said.

Odell had her own apprehensions when starting her book. “You have to go into a project like this with your eyes wide open,” she said. “It was clear to me that if I was going to take this on, I wouldn’t be writing for Condé Nast.” Despite the risks, however, people have spoken up about their fractured relationships with Wintour. “Something that struck me,” Odell noted, “is that I did not get the sense that she was that big on holding grudges.” Though Vogue was slow to put out a statement mourning Talley’s death, in January, Wintour remained in touch with him. “At the time we spoke, they had been texting, at least,” Odell told me. “They had been communicating in a way that André characterized as friendly.” For the most part—a notable exception is Joan Juliet Buck, the writer assigned to profile Asma al-Assad in 2010 then frozen out—Wintour lets her detractors be. Her power is so well-recognized that she can wield it with discretion.

And when her authority is challenged, she stays standing. In fact, in the time since the scathing Times coverage, and ensuing questions about her tenure, Wintour was promoted, to her current dual role at Vogue and its corporate parent. As for when, if ever, she might leave Vogue or Condé Nast, there’s only speculation; retirement seems increasingly unlikely. “One thing I would bring up,” Odell said, “is that she talks about Karl Lagerfeld and his longevity.” Lagerfeld worked as a designer for Chanel until his death, in 2019. As a young editor anxiously wanting to take over for Mirabella at Vogue, Wintour said she believed there should be term limits on how long one could occupy that title—five years, max. Odell’s book contains no quotes about whether Wintour believes worldwide content officers should have similar term limits.

 

Right alongside the matter of who Wintour will diminish is the matter of who Wintour will champion. Anna describes the role she played in establishing Harvey Weinstein’s credibility. She put his actresses on her covers and promoted Marchesa, the line designed by Weinstein’s wife, Georgina Chapman. Weinstein determinedly courted her approval, knowing the importance her sign-off would have. Odell writes that, after reports of his exploitative and abusive behavior were published, in 2018, Wintour had to be forcefully talked out of meeting Weinstein for lunch at his invitation. She was not, however, dissuaded from helping John Galliano, who in 2011 was caught on a cellphone camera making anti-Semitic remarks; Wintour saw to his professional rehabilitation, ensuring that he was appointed as designer of Maison Margiela.

If her critics operate in fear, her beneficiaries seem beholden. “She’s incredibly savvy,” Lee told me. “She played the game better and consolidated her power in a way I would argue has never been done at Condé Nast before.” Wintour’s relationships with major European luxury houses, which consistently advertise in Vogue—“even in hard times,” as Lee pointed out—have played a large part in establishing a perception of her as a singular force. “She continues to be elevated at Condé Nast, but over a severely depleted kingdom.”

There are questions to be raised about just what role Wintour has played in depleting the kingdom. Odell’s biography includes decisions that stalled Vogue’s growth, moments when the circulation and ad revenue of rival publications came too close to threatening Vogue’s newsstand supremacy. Condé Nast passed on a chance to acquire Net-a-Porter, now one of the world’s most highly valued luxury e-commerce sites, and Vogue delayed its transition from print to digital media far past the point when a fashion publication might have kept up with the trends of the time. Odell describes Wintour as eager to embrace the internet in theory, but slow in practice; once, when a new editor sent a welcome email to his colleagues, he received a fax from Wintour: “Joe, this is Vogue. We don’t email.” There is also the criticism that, as Wintour has consolidated her power within Condé Nast, titles under her have suffered. As Odell reports, over the course of Wintour’s career, people have often remarked on her ability to make all editorial look like her editorial; some Condé magazines, including Lucky and Glamour, have ceased print operation.

Beyond the palace intrigue of Condé there is the wider world of politics. Wintour is one of the largest fundraisers for the Democratic Party, and her coverage of Michelle Obama and Dr. Jill Biden is rivaled only by her commitment to the Clintons. She was the first editor of Vogue to put a sitting First Lady on the cover; she did so with Hillary Clinton at the apex of Bill Clinton’s impeachment scandal. But her influence is not located within one party or the other. While Teen Vogue gained attention for leaning left during Donald Trump’s presidency, Wintour insisted on having Condé staff gather for an off-the-record meeting with him. Ultimately, her political sensibility is oriented not toward swaying votes but consolidating power—power that is supported and reinforced by public fascination with her, including, notably, Odell’s book.

So formidable is Wintour’s reputation that, last year, when The New Yorker’s union authorized a strike, the unit chose to picket outside her home—even though she had no direct role in the negotiations. (Condé Nast responded by sending an internal email condemning the decision, saying it disrespected a private residence, no matter that Wintour bought her place with an interest-free $1.64 million loan from the company.) By way of explanation, Susan DeCarava, the president of the NewsGuild of New York, cited a line from The Devil Wears Prada, the novel written by Wintour’s former assistant Lauren Weisberger about “Miranda Priestly,” an obvious stand-in, and adapted into a 2006 film starring Meryl Streep. The beleaguered heroine is always being told that a million girls would kill for the job that’s killing her. “We heard it from company representatives at the table, and Guild members were living through this ‘you’re lucky to be here’ attitude,” DeCarava told me. “So, while Wintour did not have significant say in The New Yorker operations, she has profound influence over how Condé operates. In many ways she is a symbol of the gross inequality between management and workers that we’re collectively fighting to change.”

 

I purchased my first print copy of Vogue in years the way every magazine publisher must still dream of: at an airport newsstand, where I was bored and indulgent enough to spend a few dollars on what I’d already read online for free. I felt lucky it was the issue with Rihanna on the cover—a beautiful shoot, as always—and flipped through, reliving the way I used to read it: as though it were an answer to a question I hadn’t yet asked, or a window onto a landscape I dreamt of visiting. I remembered something that Stewart had said to me about the magazine: “I think of it like a metal lunchbox, or a rotary phone, or a typewriter. Something that was beloved and then abandoned. But there’s still something sentimental about it.”

That Wintour has sustained popular interest in Vogue is its own achievement. “This is the really unique thing about her,” Odell told me. “Because if you look at fashion, you don’t need Vogue to tell you what’s going on anymore. It’s so easy to come by that information online or by looking at social media.” And yet fascination with the magazine persists—a result of both tradition and Wintour’s constant, deliberate work. For all the bosses who come and go on shoes too soft to make a sound, Wintour plants a firm footprint, one that must be noticed.

Still, we should remind ourselves, often and loudly, that powerful people are only people. Their symbolic value may serve us, but we ought to let it go the rest of the time. Wintour is no exception. We have seen her demonized, humanized, and lionized by the press, sometimes all at once, with or without her voice. “She doesn’t talk about what she’s doing, and she doesn’t talk about herself very often,” Odell said. “One of her friends told me that she doesn’t want to stop working to reflect.” How much of Wintour’s public identity really exists within her control? How much of her power is in her hands, and how much is in our heads?

Part of what made The September Issue a warm, fun film was the natural tension between art, as represented by the stylist Grace Coddington, and commerce, as represented by Wintour. But on a recent rewatch I found it was not so simple as choosing sides between couture gowns and ad revenue. There’s a scene in which Coddington visits the gardens of Versailles and stands still, overwhelmed by the pristine grace of controlled nature. She looks at this symbol of a fallen monarchy not as the condition that prefigures a revolution. She sees the flowers. I wondered if the story we tell ourselves about Vogue is, ultimately, a tale of people who look at symbols of power and, in their awe, call what they see beauty.

When I asked Odell the obvious question, she said she had no idea if Wintour would read the biography. “I’m just as curious to know what she thinks of it,” Odell said. “But the book is written.”

Haley Mlotek is a writer, editor, and organizer with the National Writers Union. She is currently working on her first book, about romance and divorce.