In the capricious world of fashion, where fortunes rise and fall like hemlines, Anna Wintour's survival skills are legendary. Photo / AP
Could the Conde Nast mutiny finally bring her down?
Throughout her 34-year career at the helm of American Vogue, Anna Wintour has gathered more titles than the Queen, and weathered almost as many controversies. Installed as editor-in-chief in 1988, she has risen to become parent company Conde Nast's Artistic Director, Global Editorial Director and Global Chief Content Officer, as well as being awarded a damehood in 2017. In the capricious world of fashion, where fortunes rise and fall like hemlines, Wintour's survival skills are legendary. Why has she remained at the pinnacle for so long?
Firstly, she is both dedicated to and good at her job: you don't get to stay at the top without this being a given.
Secondly, she is surrounded by a loyal team built up over decades, with Conde Nast's board of directors continuing to support her.
Thirdly, and most pertinently, she is adroit at adapting: or at least, at seeming to adapt, positioning herself on the right side of history.
"Like all good editors, Anna is interested in everything," says Jo Elvin, who edited Conde Nast title Glamour between 2001 and 2017. "So much has changed in the way that fashion and celebrity works, but she's maintained relevance by shifting enthusiastically with those times. I remember when she put Kim Kardashian and Kanye West on the cover of Vogue in 2014. Some shook their fists at the move, and I'm sure there was a time when she would have thought such populism was 'not Vogue', but she rolled with the times and where people's fascinations lay. That's what keeps her in the game."
"She effectively exerts her own gravitational force field, magnetised by strategically deployed invitations, introductions, magazine features and messages of support," the New York Times fashion director, Vanessa Friedman, has said. Even so, the woman dubbed "Nuclear Wintour" is currently experiencing her most atomic bout of career turbulence yet. Last June, Conde Nast workers staged protests outside her Manhattan townhouse, chanting "The boss wears Prada, the workers get nada" and carrying banners saying "You can't eat prestige". Now, over 500 employees from the company – which owns New Yorker and Glamour magazines, as well as Vogue – have formed a union to push for better pay, increased job security and a stronger commitment to diversity and equality.
While Wintour is on a multi-million-dollar salary, protestors complain they are woefully underpaid, with some seeking to supplement their incomes with paid brand partnerships and sponsored posts. Wintour's camp has distanced her from these complaints - a source insisted it was a corporate issue, which is "not her thing". But could this be the scandal that dethrones her? Or will her savvy ways save her once more?
Wintour's frosty demeanour, love of fur and dextrous way of avoiding being eliminated by circumstances that would end most people's careers are more than a little reminiscent of a cat. Here, we examine her nine lives.
In February 1999, New York was rocked by Wintour's affair with Shelby Bryan, married Texas cellphone millionaire. Wintour herself had been married for 15 years to child psychiatrist David Schaffer. Both left their partners to be together, marrying in a private ceremony in 2004 (and splitting in 2020). The scandal didn't tarnish Wintour, who spent her 70th year in romantic circumstances women half her age can only dream of, by going on a string of dates with actor Bill Nighy. Whether they are still together is unclear. For such a public figure, Wintour has cannily kept her private life private.
In 2003, Wintour's former assistant, Lauren Weisberger, published The Devil Wears Prada, a barely disguised fiction drawn from her experiences working at American Vogue, which was made into a film three years later starring Meryl Streep and Anne Hathaway. Wintour allegedly said the film would "probably go straight to DVD"; it made over US$300 million. Then in one of the volte faces at which she's so adept, she praised it for making fashion "entertaining and glamorous", telling Barbara Walters that she was "100 per cent behind it" – and niftily turning up to the premiere wearing Prada. While she never forgave Weisberger for her perceived disloyalty, there's no doubt that the film gilded her image.
"Asma al-Assad is glamorous, young and very chic – the freshest and most magnetic of first ladies…" So wrote Joan Juliet Buck in a March 2011 interview with the wife of Syrian president, Bashar al-Assad. It took a year for Wintour to break her silence, noting: "We were hopeful that the Assad regime would be open to a more progressive society… but it became clear that its priorities were completely at odds with those of Vogue." The scandal passed. Wintour remained in power.
In 2012, Wintour was photographed meeting with then-disgraced designer John Galliano, who had been fired from Christian Dior the previous year after being recorded making racist and anti-Semitic comments. Her support hugely helped rehabilitate his career: after a stint in rehab, he returned to the catwalk in 2014 with a collection for Oscar de la Renta, going on to become creative director of Margiela. Wintour has been similarly loyal to other problematic fashion names, including photographers Mario Testino and Bruce Weber, both dogged by allegations of sexual misconduct (which have been strenuously denied). Whatever mud is slung, it never sticks to Wintour's shiny Teflon-coated carapace.
For decades, Wintour was as wedded to her furs as she was to her black sunglasses. In 1996, during a lunch at the Four Seasons hotel, a protestor approached her table, pulled a dead raccoon from her bag and tossed it onto her plate – barely causing her to flinch. But that was then: by 2020, she was pictured wearing "fur-free" coats by Gucci and Stella McCartney. While Elle banned fur and exotic skins from its pages last year, Vogue is yet to do so.
The annual ball at the Metropolitan Museum of Art's Costume Institute has long been self-billed as "fashion's biggest night of the year", the opening of a special yearly fashion exhibition setting the tone for the night's style. In recent years, Wintour – the chair – has been accused of "ruining" the Met Ball, with some of New York's elite complaining that she has made it too "populist". Granted, Rihanna's 2015 pizza dress might not have been to everyone's taste, but only a raging snob would disagree that Wintour's more inclusive guest list isn't a positive, even if she was forced to make it so through gritted teeth.
Once upon a time, Anna Wintour and André Leon Talley were joined at the hip, sitting side by side at shows and dinners in a manner that suggested forever friendship. But life is not a Hallmark card, and in 2018, American Vogue's most high-profile black employee fell out with Wintour after a slew of perceived professional sleights. His 2020 autobiography, The Chiffon Trenches, referred to Wintour as "incapable of simple human kindness". In an interview to promote the book, he further fanned the flames by calling her "a colonial dame", adding that "she is entitled, and I do not think she will ever let anything get in the way of her white privilege". Wintour was reportedly devastated. When Talley died in January, the two were still estranged, with Wintour further criticised for the time it took her to post a tribute.
Wintour has long been interested in politics, so when she put Kamala Harris on the cover of Vogue in January 2021, the world didn't bat an eyelid. Rather, it rubbed them, baffled. Granted, the cover was shot in lockdown, but her appearance in a black trouser suit and black Converse sneakers was widely criticised, with the internet dubbing it "disrespectful", not least when compared to the smart shift dresses worn by Michelle Obama on her covers. According to a new book by New York Times reporters Jonathan Martin and Alex Burns, Harris felt belittled by the magazine, asking aides: "Would Vogue depict another world leader this way?" When the complaint was taken directly to Wintour, she pushed back, admitting she'd chosen the cover image herself on the basis that Harris looked "relatable".
If the Vogue offices are now bastions of racial diversity, as some claim, it certainly wasn't ever thus. Throughout the Nineties and Noughties, when it came to securing a hallowed job at Conde Nast, the edict that "you could never be too rich, too thin or too white" rang true. So when Wintour was recently alleged to have uttered the words "Why are there so many white people in the room?" upon entering her Manhattan office, eyebrows were understandably raised. She also managed to exonerate herself from responsibility when the incoming editor of Teen Vogue, Alexi McCammond, resigned over racist and homophobic tweets. At the age of 72, Wintour has finally read the room, in recent months being pictured at a slam poetry event recounting "the inner voices of black men in Brooklyn", and the premiere of a documentary about BLM activist and sportsman Colin Kaepernick. Has she finally had a wake-up call – or is 'woke' simply the new black?
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