Anna Wintour had turned down requests to appear on the cover of Vogue multiple times before Meryl Streep stepped in. Annie Leibovitz
Even Anna Wintour can’t say no to Meryl Streep.
The Vogue global editorial director appears alongside Streep on the magazine’s May 2026 cover — her first time ever on the front of her own publication. But as staffers revealed on Vogue’s “The Run-Through” podcast this week, getting both women to agree was no small feat.
Wintour had turned down cover requests before, according to newly appointed head of editorial content Chloe Malle, while Streep — who covered the magazine in 2012 and 2017 — “felt like an automatic no.”
Vogue staffers spilled the behind-the-scenes details of the May 2026 cover shoot on the magazine’s “The Run-Through” podcast this week. Getty Images
Both women wear custom Prada on the cover — or as Malle put it, “two devils, two Pradas.” Getty Images
Head of editorial content Chloe Malle first pitched the idea to Wintour during Paris Fashion Week in October. Getty Images
With “The Devil Wears Prada 2” arriving May 1, Vogue wanted a cover to match the moment, but Hathaway had already appeared on the August issue and Blunt had her own covers in the works.
Malle floated the idea of a shared cover to Wintour during Paris Fashion Week last October, shortly after Malle was promoted into her role. “I said, ‘Well, Anna, it would be kind of amazing to do you and Meryl on the cover,’” Malle recalled. “And she said, ‘Well, Chloe, that’s very flattering, but it’s just not my style.’”
Then Streep apparently asked — “and it was a different answer. So we see who has the power of persuasion.”
In the cover story itself, Malle wrote that the efforts required “not a small bit of arm-twisting.”
Both women — the fictional Miranda Priestly and her real-life inspiration — wear custom Prada on the cover, or as Malle put it: “Two devils, two Pradas.”
The shoot, photographed by Annie Leibovitz and styled by Grace Coddington, was kept under extreme secrecy for months; Malle said the project “made the Pentagon papers look like Richard Scarry books.”
Virginia Smith, Vogue’s director of global fashion network, called in all the clothes solo to avoid raising suspicion, describing her outreach to designers as “a puzzle of vague references to shoots and then out-and-out lies.”
Annie Leibovitz photographed the shoot; she, Streep and Wintour are all 76 years old and born in the same year. Getty Images
Vogue kept the cover under wraps for months, with only a handful of staffers in the know. Getty Images
Grace Coddington styled the shoot and had to be secretly smuggled into Vogue’s offices to avoid suspicion. Getty Images
Coddington had to be smuggled into Vogue’s offices for the fitting. “Anna felt that having Grace here would be suspicious,” Smith said. “So I had to hide Grace and get her into a little area of a fitting room without anyone seeing her.”
Despite the cloak-and-dagger logistics, the two cover stars hit it off easily. Smith said that on a freezing fitting day at the Crosby Hotel, Streep and Wintour walked in wearing matching sunshine yellow scarves — completely unplanned. “Anna was so excited, she said, ‘You have to take a picture,’” Malle recalled.
The cover lands just ahead of “The Devil Wears Prada 2,” in theaters May 1 — the same week Wintour hosts the Met Gala.
Streep’s Miranda Priestly was famously inspired by Wintour, and the editor has been embracing her devil reputation all year, from a cheeky Oscars bit with Hathaway to a reunion with Streep at Milan Fashion Week last fall.
“People have made millions and millions of dollars on the book, the movie … all based on Anna” a source told Page Six. “Why shouldn’t Anna have some fun with it too?”