Anna Wintour and Meryl Streep appear together on the cover of Vogue’s May 2026 issue, marking the first time in the magazine’s 134-year history that its editor-in-chief has starred on its own cover. The issue, photographed by Annie Leibovitz and styled by Grace Coddington, hits newsstands April 28 — three days before The Devil Wears Prada 2 opens in theaters nationwide.
Image: Courtesy of Vogue / Annie Leibovitz
The pairing is no coincidence. Streep’s Miranda Priestly — widely understood to be inspired by Wintour — returns in the long-awaited sequel, making the joint Vogue cover a savvy piece of cross-promotion for both Condé Nast and 20th Century Studios. It’s also a rare moment of self-awareness from Wintour, who has led Vogue for 37 years without once putting herself on the front page.
The Cover: What Wintour and Streep Are Wearing
Both women wore Prada for the shoot — a notable PR win for the Italian house amid a busy 2026 celebrity campaign cycle that includes Bella Hadid’s Prada ambassador role and Prada’s Re-Nylon 2026 campaign.
Wintour appears in a tailored navy Prada suit paired with a crisp white blouse, her signature Chanel sunglasses (the brand is deep into its own 2026 campaign with Margot Robbie), Manolo Blahnik shoes, and S.J. Phillips necklaces. Hair was styled by Bobby Michael; makeup by Melissa Silver.
Streep wears a red Prada ensemble featuring a flowing pleated skirt with a structured top. Her hair and makeup were handled by Donald S. McInnes. The result is a cover that balances Wintour’s editorial precision against Streep’s Hollywood presence — both in the house of Prada, both very much in character. Sadie Sink in custom Prada at the West End earlier this year underscores just how dominant the label’s celebrity dressing strategy has become in 2026.
Inside the Issue: Wintour and Streep in Conversation With Greta Gerwig
The accompanying feature interview was conducted by filmmaker Greta Gerwig, the Barbie director currently in production on a new project. The conversation spans fashion, leadership, friendship, and the Devil Wears Prada sequel.
“First of all, I’d like to say it’s such an honor to be played by Meryl, however distant Miranda is from myself. Who wouldn’t think that that wasn’t the most extraordinary gift?”
— Anna Wintour, Editor-in-Chief, Vogue
Streep, for her part, discussed how she approached returning to Miranda Priestly after 20 years. “This time we pared her down. We made her simpler and just more essentially her,” Streep told Gerwig. She also reflected on researching Wintour for the original role: “I did think honestly about Anna and tried to imagine what it was like to carry her responsibility and to be as interested in the world and curious as she must have to be.”
The Hollywood Reporter noted that Streep also made remarks referencing Melania Trump during the interview, though the full context of those comments awaits the issue’s publication. Digital subscribers can access the full interview now.
The Devil Wears Prada 2: Release Date, Cast, and Plot
The Devil Wears Prada 2 opens May 1, 2026 via 20th Century Studios. Director David Frankel and screenwriter Aline Brosh McKenna both return from the 2006 original. The film sees Anne Hathaway and Meryl Streep reunite as Andy Sachs returns to Runway magazine, where Miranda Priestly is navigating digital disruption and the publication’s survival in a transformed media landscape.
The returning cast includes Emily Blunt and Stanley Tucci. New additions feature Kenneth Branagh, Simone Ashley, Justin Theroux, Lucy Liu, Lady Gaga, Pauline Chalamet, B.J. Novak, and a cameo by Donatella Versace. Full cast and crew details are available on The Devil Wears Prada 2 on IMDb.
Blunt’s Emily now runs a luxury brand that could fund Runway’s future — a plotline that mirrors real-world tensions between legacy print media and the digital economy. Several major Devil Wears Prada 2 brand collaborations, including tie-ins with L’Oréal, Diet Coke, and Grey Goose, are already in market.
Vogue May 2026: On Newsstands April 28
The Anna Wintour Meryl Streep Vogue May 2026 cover issue arrives on newsstands nationwide on April 28. It is the first time a sitting Condé Nast editor has appeared on the cover of their own publication in the company’s history.
The timing puts the cover at the center of a packed May fashion calendar. Met Gala 2026 follows days later, and both events position Wintour firmly at the intersection of fashion, film, and celebrity culture heading into the summer season. For more on the season’s biggest celebrity fashion moments, see our coverage of the Vanity Fair Oscar Party 2026 fashion.
