Anna Wintour has always been enigmatic.
As a result, she hasn’t even told anyone about her recent Oscar appearance with Anne Hathaway in The Devil Wears Prada, and has yet to reveal whether she’s making a cameo appearance in the film’s long-awaited sequel, a source told Page Six.
But after watching an entire multi-million dollar brand grow from a hit book by Lauren Weisberger, Wintour’s assistant at Vogue from 1999 to 2000, the legendary editor is now determined to enter the pop culture fray.
She finally accepted her reputation as a “devil”.
“People have made millions of dollars from books and movies about Anna,” said one fashion insider. “Why don’t you have some fun, Anna?”
What is clear is that the high priestess of magazine publishing is now firmly on board with the film’s promotion. The film will be released in theaters on Friday, May 1st, just three days before the Met Gala, which she will host. The Met Gala brings together some of the biggest names in fashion and celebrities to raise money for the Anna Wintour Costume Center.
Officials credit Wintour with realizing that adding a sense of humor to Romain à Clef humanized her, honed her heritage and brought more positive attention to the Met Gala.
Former Vogue editor-in-chief William Norwich, who is widely considered to be the inspiration for Stanley Tucci’s incomparable character Nigel Kipling, said: “Anna Wintour walks on water in high heels, but it’s not as easy as you think. She has a great sense of humor and is at a fun time in her life.”
The 76-year-old Brit was all smiles at Milan Fashion Week last fall when he greeted Meryl Streep, who plays Wintour’s thinly veiled Miranda Priestly in Prada. And Wintour played her part to the end when she jokingly appeared alongside The Devil Wears Prada star Anne Hathaway at the Oscars earlier this month to announce the winner for Best Costume Design.
“Some might argue that your real-life wardrobe is important, too. Will you look elegant and glamorous on Hollywood’s most important night, when the most important people in the fashion industry are judging your appearance?” Hathaway says, shivering in character, while Wintour turns away, donning her trademark sunglasses. “Anna, I’m just curious, what do you think of my dress tonight?”
Without missing a beat, Winter answered coldly: “And the candidates are…”
There was more laughter from the A-list crowd when Wintour called Hathaway “Emily,” the name of Priestley’s assistant.
Sources said Wintour was not paid any money to promote the film, but one industry insider noted that she has always been sensitive to the “zeitgeist.”
And she definitely seemed to be enjoying being feted not only at the Oscars ceremony, but also at the Vanity Fair gala afterwards, where she was joined by one of her closest friends, Hillary Clinton aide Huma Abedin.
“Anna always loves a good story. It’s part of the culture and it’s fun. It’s Meryl, it’s Anne, it turned out to be something smartly done and everyone loved it,” one source said. “It brings me joy when I need it.”
When asked if Winter would be in the sequel, a source said, “She might be. I’d be surprised if she was, but she’s been surprising people a lot lately.”
Norwich said he wouldn’t be surprised if Wintour made a cameo appearance, noting that she became “very close” to Streep, especially through the New York theater world.
The first film, released in May 2016, was a huge success, grossing over $326 million worldwide for a production cost of approximately $40 million.
The sequel is expected to gross more than $55 million in its domestic opening weekend, and filmmakers Disney and 20th Century Studios have signed a slew of big-money brand deals, partnering with L’Oréal Paris, Tweezerman, Tresemme, Diet Coke and Target, among others.
Mr. Weisberger was a Columbia University graduate in his early 20s when he joined Winter’s staff in December 1999, but left before the end of 2000. When she sold The Devil Wears Prada to Doubleday in May 2002 for $250,000, Wintour, who typically had three assistants on hand at any given time, couldn’t even remember who Weisberger was.
“She said, ‘I don’t remember him,'” former Vogue editor-in-chief Laurie Jones told Page Six. “I described her as tall and willowy blonde, but that didn’t differentiate her from many of the other women at Vogue. Lauren hadn’t worked there long enough for Anna to remember her.”
When the book was released in February 2003, it was a huge hit. However, despite rumors to the contrary, Winter was not too upset by this story. The story follows Andy Sachs (Hathaway in the film), an aspiring journalist who begins working for the domineering editor-in-chief of the fictional magazine Runway.
“I remember Anna reading the galleys for the book, and she wasn’t angry,” Jones said.
In fact, Jones recalled that Wintour wore Prada to a special screening of the first film before its release. “She treated this like fun… from the beginning.”
However, there is one thing that has changed thanks to this book.
“I had to sign a non-disclosure agreement at Condé Nast,” Jones revealed. “It’s pretty standard now, but it became policy after Lauren’s book came out.”
Regardless of Wintour’s own thoughts, many in the fashion world were worried that making the film would upset her.
“There was a lot of fear surrounding the movie,” fashion writer Amy O’Dell, author of “Anna: A Biography,” told Page Six. “The director, David Frankel, told me that the reason the gala scenes were shot at the Museum of Natural History was because everyone in New York City was afraid. It was the only place where she wasn’t under influence.”
And it wasn’t just the Metropolitan Museum of Art, home to the Anna Wintour Costume Center (named after her in 2014). Frankel was unable to photograph at the Museum of Modern Art. Because the people on the board had ties to Winter and were afraid of her. So was Bryant Park, then the home of New York Fashion Week.
Designers were even nervous about lending costumes to legendary stylist Patricia Field for the film. Couture houses were reluctant to lend their work for fear of upsetting the powers that be in Vogue.
“[Originally]there weren’t any notable designers that would be in this movie. They just didn’t want to anger[editor-in-chief]Anna[Wintour],” Frankel told Entertainment Weekly. “I think it was Prada who helped break her nerves and told Anna that she wasn’t going to be upset.”
Director Field said Miranda Priestly’s film version was never written to be a “bitch”. When asked if Wintour was the inspiration for Streep’s character, she told Page Six: “Inspiration comes from several places: from the actors, and from the demands of the script.”
Last year, Wintour finally revealed what she really thought about the comparisons to Streep’s Miranda Priestly.
Despite reading the book, Wintour told New Yorker editor David Remnick in an interview on The New Yorker Radio Hour podcast: “I went to the premiere wearing Prada, and I had no idea what the movie was going to be about. And I think the fashion industry was very nice and concerned about this movie for me. I thought it was going to paint me in a kind of difficult light.”
However, her reaction was completely different.
She felt that the film had “a lot of humor, it was witty, it had Meryl Streep in it…I thought it was a fair shot in the end.”
Wintour is no longer Vogue’s editor-in-chief, handing over that title to Chloe Malle last year, and is now Condé Nast’s global chief content officer and Vogue’s global editorial director.
But Rachel Richardson, author of culture and trends newsletter Highly Flammable, said that far from regressing, Wintour seems to be “leaning toward stardom and attracting more attention than ever.”
“People know in their bones that Miranda Priestly is Wintour, so why shouldn’t she be in on the joke and have the benefit of being immortalized in Hollywood?” Richardson said. “This movie portrays Priestley as an icon, flawed but an icon nonetheless. That really lends itself to Winter’s image… Her involvement so far also suggests she might make a cameo in the movie, so keep an eye out.”
Sources say Wintour was indeed on set in Milan and, as we revealed, Oscar-winning filmmaker Fisher Stevens is following her for a Vogue documentary.
“The[first]movie became such a phenomenon and people love it so much. It’s a classic at this point and it makes sense for Anna to lean into it,” O’Dell said, adding that the film also overshadows many of the controversies that Wintour has been embroiled in over the past few years.
She has responded to harsh criticism for not doing enough to support diversity and was accused of creating a toxic work environment for Black employees. Meanwhile, her former close friend, the late Vogue editor Andre Leon Talley, described her in his 2020 book, The Chiffon Trench, as a “ruthless” and “colonial” person incapable of simple human kindness. They reconciled before his death in January 2022.
“She’s been subject to a lot of controversy over the last few years, but this is what people love about her,” O’Dell said, “That’s what turned her into ‘Anna’ — and that’s what sets her apart from other editors…Meryl Streep played her, and that turned her into this huge A-list celebrity. You have to imagine her watching that.”
Additionally, with Condé Nast experiencing “constant layoffs” due to the closure of publications such as Teen Vogue, the company’s union “uproar” amid layoffs, and complaints about Jeff Bezos paying for this year’s Met Gala, “it makes sense for[Winter]to create excitement around this film,” O’Dell said.
“This film will be released on the Friday before the gala, and I think Anna will do much, much more than Bezos to remind people about the fashion industry they love and what it’s all about. People are so excited about this film… She can’t be beat.”
