Vogue’s May cover: Streep + Wintour

Vogue’s May 2026 cover turned a long-running fashion in-joke into an official photo shoot by putting Meryl Streep beside Anna Wintour, the editor whose image helped shape Streep’s 2006 character Miranda Priestly in *The Devil Wears Prada*. The cover story was photographed by Annie Leibovitz and styled by Grace Coddington, which made the whole package feel like a reunion of fashion power centers, not a normal celebrity profile. (vogue.com) The timing was not accidental. Vogue published the issue days before *The Devil Wears Prada 2* reaches theaters on May 1, 2026, and 20th Century Studios is already promoting the sequel with official stills and trailers featuring Streep, Anne Hathaway, Emily Blunt, and Stanley Tucci. (vogue.com) (20thcenturystudios.com) (deadline.com) That pairing works because the original movie always sat halfway between fiction and fashion gossip. Lauren Weisberger’s 2004 novel was written after she worked as Wintour’s assistant at Vogue, and the 2006 film turned that office mythology into one of Hollywood’s most durable fashion stories. (vogue.com) (pagesix.com) Vogue leaned straight into that overlap instead of pretending it does not exist. The interview was framed by Greta Gerwig, and Wintour and Streep talked not only about clothes and work but also about children, grandchildren, and the way public personas harden into characters over time. (vogue.com) (abcnews.com) One reason the cover landed so fast is that Anna Wintour’s job changed recently, which gave the images an extra layer. After leading American Vogue from 1988 to 2025, she moved into broader Condé Nast roles as global chief content officer and artistic director, so this shoot also reads like a post-editor-in-chief self-portrait. (abcnews.com) (goodmorningamerica.com) The sequel gives that self-portrait a second engine. Trade reports say the new film follows Miranda Priestly as she navigates the decline of print magazines, which means the fictional plot now circles the same industry pressures that reshaped real magazines over the last decade. (variety.com) (deadline.com) So the Vogue package is selling two reunions at once. It brings back Streep’s most famous fashion role just as the sequel opens, and it brings Wintour back into the center of the magazine image machine she spent nearly four decades building. (vogue.com) (abcnews.com) That is why the cover spread traveled beyond fashion media so quickly. Readers were not just looking at a May issue of Vogue; they were looking at the real editor, the actress who played her shadow, and a sequel campaign arriving at the exact moment nostalgia for 2006 has become a full studio release strategy. (usatoday.com) (20thcenturystudios.com)