Anna Wintour has always been inscrutable.
So much so that she didn’t even tell people around her about her recent Oscars appearance with “The Devil Wears Prada” star Anne Hathaway — and hasn’t yet revealed to them if she’s made a cameo in the movie’s much-anticipated sequel, sources told Page Six.
But after watching an entire multi-million dollar brand grow around Lauren Weisberger’s hit book — based on her time as Wintour’s assistant at Vogue from 1999 to 2000 — the legendary editor has now deigned to enter the pop culture fray.
She’s finally embraced her reputation as the “devil.”
“People have made millions and millions of dollars on the book, the movie … all based on Anna” said one fashion source. “Why shouldn’t Anna have some fun with it too?”
What is clear is that the high priestess of magazine publishing is now firmly part of the promotion for the movie, which arrives in theaters on Friday, May 1 — just three days before she hosts the Met Gala, where the biggest names in fashion and celebrity mingle to raise funds for the Anna Wintour Costume Center.
Insiders credit Wintour for realizing that having a sense of humor about the roman à clef humanizes her, burnishes her legacy and brings more positive attention to the Met Gala.
Former Vogue editor William Norwich, widely thought to be the inspiration for Stanley Tucci’s incomparable character Nigel Kipling, told Page Six, “Anna Wintour walks on water in high heels and that’s not as easy as you think it is. She has a great sense of humor and she’s at the stage of her life where she’s having fun.”
The 76-year-old Brit was all smiles when she greeted Meryl Streep — who plays Miranda Priestly, a thinly veiled copy of Wintour, in the “Prada” movies — at Milan Fashion Week last fall. And Wintour played her role to the hilt when she joined “Devil Wears Prada” star Anne Hathaway for a tongue-in-cheek appearance at the Oscars earlier this month, announcing the winner for best costume design.
“One could argue that one’s wardrobe in real life is also key. Does it make one appear elegant and attractive on, say, the most important night in Hollywood when, say, the most important people in fashion will be judging how one looks,” Hathaway, trembling in the guise of her character, said, while Wintour donned her trademark sunglasses and turned away. “Anna, just curious — what do you think of my dress tonight?”
Without skipping a beat, Wintour icily replied: “And the nominees are …”
There was further laughter from the A-list crowd when Wintour called Hathaway “Emily,” the name of Priestly’s assistant.
Wintour is not being paid for any movie promotion, sources confirm, but one industry insider noted that she has always been savvy at tuning into the “zeitgeist.”
And she certainly seemed to enjoy being feted at the Oscars as well as the Vanity Fair bash after, where she was joined by one of her besties, Hillary Clinton aide Huma Abedin.
“Anna always loves a good story. This is part of the culture and it’s fun — it’s Meryl, it’s Anne, it turned into something that was smartly done and everyone loved it,” one insider said. “It brings fun just when we need it.”
Asked if Wintour makes an appearance in the sequel, the insider replied, “She may have. I would be surprised if she had — but she’s surprised people a lot lately.”
Norwich said he would not be surprised if Wintour had a cameo, revealing she has become “very close” with Streep, particularly through New York’s theater scene.
The first movie, which premiered in May 2016, was a major box office success, grossing over $326 million worldwide against a production budget of approximately $40 million.
The sequel is forecast to pull in more than $55 million for its domestic opening weekend and the moviemakers, Disney and 20th Century Studios, have signed dozens of big-money branding deals to tie in, including with L’Oréal Paris, Tweezerman, Tresemmé, Diet Coke and Target.
Weisberger was a Columbia University graduate in her early 20s when she joined Wintour’s staff in December 1999, leaving before the end of 2000. When she sold “The Devil Wears Prada” in May 2002 to Doubleday for a reported $250,000, Wintour — who typically had three assistants at any time — could not even recall who Weisberger was.
“She said ‘I can’t remember that girl,’” Laurie Jones, the former managing editor at Vogue, told Page Six. “I described her as a tall, willowy blonde, but that didn’t distinguish her from many others at Vogue! Lauren had not worked there long enough for Anna to remember her.”
When the book came out in February 2003 it was a hit. But, despite rumors to the contrary, Wintour was never very upset with the story — which tells the tale of aspiring journalist Andy Sachs (Hathaway in the movie), who goes to work for the tyrannical editor-in-chief of the fictional Runway magazine.
“I remember Anna reading the galleys of the book when it came in. She wasn’t angry,” said Jones.
Indeed, Jones recalled that Wintour even wore Prada to a special screening of the first movie before its release. “She treated this with some amusement … from the beginning.”
Although one thing has changed as a result of the book.
“We did have to sign non-disclosure forms at Condé Nast,” Jones revealed. “That’s pretty standard now, but it became policy after Lauren’s book came out.”
Regardless of Wintour’s own thoughts, many in fashion were worried about upsetting her when it came to making the movie.
“There was a lot of fear around the film,” fashion writer Amy Odell, author of “Anna: The Biography,” told Page Six. “The director, David Frankel, told me the reason the gala scene was filmed at the Museum of Natural History was because everyone in NYC was afraid. It was the only place they could find where she had no influence.”
And it wasn’t just at the Metropolitan Museum of Art, home of the Anna Wintour Costume Center (it was named for her in 2014). Frankel couldn’t film at the Museum of Modern Art because people on the board were affiliated with Wintour and afraid of her. The same went for Bryant Park, where New York Fashion Week was headquartered at the time.
Designers were even nervous to loan legendary stylist Patricia Field clothes for the movie. couture houses hesitated to lend pieces for fear of upsetting the powers that be at Vogue.
“There were [initially] no designers of note who would appear in the film. They just didn’t want to incur the wrath of [editor-in-chief] Anna [Wintour],” director Frankel told Entertainment Weekly. “I think it was Prada that helped her break the ice and said that Anna’s not going to be upset.”
Field said that the film version of Miranda Priestly was never written to be “bitchy”. Asked if Wintour was her inspiration for Streep’s character, she told Page Six, “You get inspiration in a few different places, one being the actor and then the demands of the script.”
Last year, Wintour finally revealed her true thoughts on the comparisons between her and Streep‘s Miranda Priestley.
Despite the fact she had read the book, Wintour told New Yorker editor David Remnick on “The New Yorker Radio Hour” podcast: “I went to the premiere wearing Prada, completely having no idea what the film was going to be about. And I think that the fashion industry were very sweetly concerned for me about the film, that it was going to paint me in some kind of difficult light.”
However, her reaction was quite different.
She found the film “had a lot of humor to it. It had a lot of wit. It had Meryl Streep … In the end, I thought it was a fair shot.”
Wintour is no longer editor of Vogue, having passed that title on to Chloe Malle last year, and is now Global Chief Content Officer for Condé Nast and Global Editorial Director of Vogue.
But Rachel Richardson, who writes the culture and trends newsletter Highly Flammable, pointed out that — far from stepping back — Wintour seems to be “leaning into being a star and is more visible than ever”.
“People know in their bones that Miranda Priestly is Wintour, so why shouldn’t she be in on the joke and get the benefit of being immortalized in Hollywood?” Richardson said. “The film portrays Priestly as an icon. Flawed, but an icon nonetheless. That helps Wintour’s image enormously … her involvement thus far also suggests to me that she may have a cameo in the movie, so keep your eyes peeled.”
Wintour did, in fact, make a visit to the set in Milan, sources told us, and as we revealed, she is being followed by Oscar-winning filmmaker Fisher Stevens for a documentary about Vogue.
“The [first] film became such a phenomenon, people love it so much. It’s a classic at this point, that it only behooves Anna to lean into it,” said Odell, who added that it also overshadows much of the controversy that Wintour has found herself in over the past few years.
She has been heavily criticized for not doing enough to support diversity, which she copped to, and was accused of creating a toxic work environment for black employees. Meanwhile, the late Vogue editor André Leon Talley, a onetime close friend, dubbed her a “ruthless” and “colonial” figure incapable of simple human kindness, in his 2020 book “The Chiffon Trenches.” They did make up before his death in January 2022.
“She’s been surrounded by so much controversy over recent years and this is something that people love,” said Odell, “It turned her into ‘Anna’ — and it distinguishes her from other editors … Meryl Streep played her and it turned her into this huge A-list celebrity. You have to imagine she sees that.”
Plus, with Condé Nast “constantly being whittled down” with the closure of publications like Teen Vogue, the company’s unions “making noise” amid layoffs, and complaints about Jeff Bezos paying for this year’s Met Gala, “it makes sense [for Wintour] to create a fervor about this film,” said Odell.
“It comes out the Friday before the Gala and I think Anna would much, much rather remind people about the fashion industry they love that and its lure than Bezos. People are so excited about this movie … she can’t lose.”
