Most people’s image of Anna Wintour is in fact that of Meryl Streep – her portrayal of the brutal glossy magazine editor Miranda Priestly in the 2006 film The Devil Wears Prada made for a veritable meme machine. Killer put-downs included: “Details of your incompetence do not interest me”; “Please bore someone else with your question”; “By all means move at a glacial pace – you know how that thrills me.”
But the real Anna Wintour – editor-in-chief of Vogue and chief content officer of Condé Nast – is a far more complex and surprising character.
On Monday night Wintour will host the Met Gala, as she has done every year since 1995. This year’s theme and guests make this the most aggressively anti-Maga event since Trump’s inauguration. As the White House sinks its teeth into diversity, equity and inclusion, Wintour has built this year’s Gala around “black dandyism”, inviting actor Colman Domingo, F1 driver Lewis Hamilton and singer Pharrell Williams to co-chair the event. Monica Miller, whose 2009 book Slaves to Fashion inspired the evening, called it “an incredibly political moment”.
The theme and accompanying exhibition were planned before the election, but Wintour was a crucial Democratic fundraiser. She helped pull in tens of millions of dollars in 2024, including a single evening in New York that collected $25m for Biden. This is not a Trump-friendly crowd – and it will be the biggest celebrity event of the year.
“Red carpet events in general are in decline,” says Amy Odell, author of Anna: the Biography.
“People aren’t watching the Oscars any more, but the Met Gala goes round the world. Everyone knows that if you walk that carpet, you’re going to be exposed to people who could be important for your career or your bank balance. That’s how she’s got the price of seats up from $5,000 to $75,000, which is incredible and speaks to her business acumen.”
That Wintour can still create the event of the year in fashion and celebrity after 30 years at the helm is remarkable. That, in her role at Condé Nast, she is overseeing 1 billion consumers in 32 countries is an astonishing achievement. That she is, in effect, the chief content director of the $1.85tn fashion industry – roughly 1.6% of global GDP – is staggering. It’s entirely unsurprising that when she was made a Companion of Honour at Buckingham Palace in February, she told King Charles she had no plans to stop working. Some wish it weren’t so – such is the overwhelming effect of her influence on Condé Nast’s stable of magazines.
“Bernard Arnault [chief executive of fashion giant LVMH] and Anna Wintour are the two most important people in the fashion industry,” explains Lauren Sherman, who writes about that world for the insider tip sheet Puck. “She’s good at being in charge, and at having authority and an opinion. There is something about people attracted to this industry where they’re supposed trendsetters – they are usually followers. She’s a leader. People can hate her – in the 90s, they really did – but the reality is: they need her.”
Wintour’s legend includes outlandish myths, but the truth is still extraordinary. Her famous sunglasses are prescription but she admits to using them as a disguise – in the front row at fashion shows, nobody can tell if she’s frowning. Her routine is regimental. At her Greenwich Village townhouse, she is up between 4.30am and 5am on weekdays; she reads the US and UK papers then exercises (usually a tennis lesson) before arriving at work at 7am. Breakfast is usually coffee. It is said that her “go-to” lunch is a steak and caprese salad without the tomatoes; how can it be a caprese salad without the tomatoes? If Anna Wintour says so, that’s how. Daily meetings are short, and she leaves at 5pm with a “take-home” work bag.
Wintour herself has a neat line in self-deprecation. On David Letterman in 2022 she rattled off some common myths: “I’m an ice queen, I’m the sun king, I’m an alien fleeing from District 9 and I’m a dominatrix, so I reckon that makes me lukewarm royalty with a whip from outer space.”
And yet, Odell reports, the rigid, dress-code Vogue of years gone by has melted away and a softer Wintour is emerging. This may have something to do with the actor Bill Nighy, with whom she has a close platonic friendship. She still obsesses over details – like banning certain foods from the Met Gala meal (they get stuck in people’s teeth). But at home, when her children, grandchildren and friends come over, she plays tennis and “stupid games”. “That’s my solace,” she told the Financial Times.
At the weekend she heads to Mastic, Long Island, where her Hamptons home is a small collection of old buildings set among 40 acres of carefully designed wild gardens. It’s in a place described by the New York Times as “on the wrong side of the highway to the Hamptons, in a modest town unfashionably distant from the area’s white-sand beaches”.
There she will wear jeans, flats, no makeup, unload the dishwasher and change her grandchildren’s nappies. Her children with her late former husband, child psychiatrist David Shaffer – Charles, 40, and Bee, 37 – have three children between them. The house boasts a barn for dinner parties and after-dinner games.
Wintour has always rigidly divided her work and family time. Stephanie Winston Wolkoff, former director of special events for Vogue, recalls going bowling with Anna and Bee, and being surprised to find both wearing bowling shoes and clowning around. Yet when they got back into the office it was as if that evening had never happened.
The daughter of the former Evening Standard editor Charles Wintour, known to his staff as “chilly Charlie”, she studied at the North London Collegiate School, rebelling against the dress code by taking up the hemlines of her skirts, prompting her father to suggest she become editor of Vogue.
And so it seems her destiny was set. She left school at 15 for a job at fashion boutique Biba, then worked as an assistant at Harper’s Bazaar and Harper’s & Queen in London. Wintour relocated to New York in 1975 as junior fashion editor at Harper’s Bazaar, became creative director of American Vogue and went on to edit British Vogue. She took charge of the US fashion bible in 1988.
“Even as a stylist she fused culture with fashion,” says Odell. “That was her innovation and that’s the world we live in – art, celebrities and fashion entwined. The Met Gala is an exemplar of that fusing culture, capitalism and commerce with fashion.”Even now Vogue’s combined print and digital circulation in the second half of 2024 was 1.2m, according to the Alliance for Audited Media. In an age of collapsing print titles, it’s astonishing to compare this with 2007, when the September issue was the magazine’s most profitable ever, and sold… 1.2 million copies. Since 2000, circulation has been pretty level under her reign. In this day and age, that is another staggering achievement.
As for Miranda Priestly, Streep confessed she based the character more on Clint Eastwood than Wintour – the soft voice, the killer lines. Sadly, we never got to see Miranda in a gunfight. Maybe next year’s Met Gala theme?
