I remember attending the New York premiere of The Devil Wears Prada with my mother. I wore my prom dress—a sage-green beaded ’20s shift from the Paris flea market—and we sat behind Anna (in…Prada) and her daughter, Bee. Bee and I were both in college and discussed our summer plans.
Years later, when the team at Vogue learned about the forthcoming sequel, we all felt strongly that Disney shouldn’t be allowed to have all the fun. The Devil Wears Prada 2 conveniently hits theaters the weekend before the Met Gala, so if we wanted a cover tied to the film, it would need to be May’s. But who to ask? Should it be Meryl? Or what if we asked both “Mirandas”—Anna and Meryl?
Read Vogue’s May 2026 cover story, featuring Meryl Streep and Anna Wintour, here.
In early October, I was sharing the backseat of Anna’s towncar in Paris, gliding up the Rue Capucines to a Balenciaga preview. Discussing spring covers, we got to May, and I gingerly asked, “Would you ever consider being on the cover with Meryl?” An amused curl of a smile, but she didn’t look at me. “That’s very flattering, Chloe, but it’s not really my style,” she said. Well, I thought, I tried. Months later, it turned out to be Meryl who finally convinced her, and I am so grateful. What a way to memorialize a moment in our culture!
When I started working at Vogue some years after that 2006 premiere, friends’ parents, suburban businessmen, and my mom’s doormen would all ask, “Is it like that?” “What’s the most Devil Wears Prada thing that’s happened?” “What’s it like working for Miranda Priestly?” It amazed me how universal this book and film had made Anna and, consequently, Vogue. These were people outside of fashion—men especially. As it happens, Miranda is the role that men most ask Meryl about and see themselves in.
This was just one of the unexpected tidbits from the Meryl-Anna interview accompanying Annie Leibovitz’s cover shoot—a three-way conversation conducted by Greta Gerwig (Meryl’s very good idea!). Topic A was The Devil Wears Prada 2. What made Meryl want to do the sequel? What did Anna do when she heard it was happening? (Answer: She called Meryl.) Meryl revealed she would never actually want Anna’s job (“I would dread the shoes”). Nor could Anna imagine doing Meryl’s (“There’s no way”).
I was there to keep things on track but really I just enjoyed myself. They talked about longevity among designers, dressing for work, how clothes express who we are (who can forget Miranda’s cerulean sweater monologue?). This made me think about “Costume Art,” the upcoming Costume Institute exhibition at The Metropolitan Museum. Elsewhere in the issue, Ethan James Green has photographed fashion and fine art for us inside The Met’s new Condé M. Nast Galleries; Annie assembled members of the Gala host committee for portraits; five visual artists considered the range of body types in the exhibition; and we staged a pajama party at The Mark Hotel to honor the tradition of seeing the sun rise after a very late night in ball gowns.
Annie photographed her fellow septuagenarians (incredibly, she, Anna, and Meryl are all 76—as is Miuccia Prada!) at a studio in Red Hook under the darkest cloak of secrecy. This was imperative to us all, but mostly Anna. She treated our cover like the Pentagon Papers, even shushing The Gilded Age star Louisa Jacobson—Meryl’s youngest daughter—when Louisa happily brought the whole thing up front row at Calvin Klein. With sittings editor Grace Coddington, Virginia Smith did store pulls at Dries Van Noten and Prada and traveled with the clothes to set, loading and unloading the trunks herself. Anna’s assistants, Emily and Caroline, were also read into the plan and helped along the way—fitting, considering the subject at hand.
Amid it all, I had the thought: Why not make our second Replica Handbag Store Book Club pick The Devil Wears Prada? I’d never actually read Lauren Weisberger’s 2003 novel, and it is a wild ride: five-inch stilettos every day, bottomless corporate car accounts, and New York coffee that, apparently, cost $1 a cup! We’ll be hosting an early screening of the film for our book club and friends of Vogue and I’ve made it my mission to invite as many former assistants to Anna as we can find. That’s all.
