Anna Wintour spent two decades refusing to acknowledge that The Devil Wears Prada had anything to do with her. Now she's starring in the sequel's marketing campaign. That shift — from icy denial to enthusiastic participation — tells you almost everything you need to know about where fashion, celebrity, and cultural power stand in 2026.
The Devil Wears Prada (film) sequel opened in theaters on May 1, 2026, bringing back Meryl Streep, Anne Hathaway, Emily Blunt, and Stanley Tucci — and, in the strangest twist, the woman the whole thing was always secretly about.
The Sequel Nobody Thought Would Happen — But Everyone Needed
Twenty years after the original film became a cultural landmark, The Devil Wears Prada 2 arrives at a moment that feels almost engineered to receive it. The sequel's plot centers on the decline of print media: Runway magazine is facing layoffs and weighing whether to sell itself to an oligarch. That premise isn't satire — it's practically a documentary treatment of what has happened to legacy fashion publishing, including Vogue itself.
The original film was based on Lauren Weisberger's novel, which drew from her 10 months working as Wintour's assistant in 1999. The book sold 13 million copies, and the 2006 film became one of the most quotable comedies of the decade. Streep's Miranda Priestly — imperious, brilliant, impossible — became one of cinema's great villains, and everyone assumed it was a thinly veiled portrait of Wintour.
Wintour consistently denied the connection, at least in public. She described the film as "fun" and gave carefully non-committal interviews. But she never fully embraced it, and the industry followed her lead: when the original film was in production, designers refused to lend clothes, and director David Frankel was barred from filming at the Met Gala, Bryant Park, and MoMA — a form of soft blacklisting that could only have come from one place.
Anna Wintour's Calculated Pivot: From Villain to Co-Conspirator
For the sequel, everything is different. Wintour not only cooperated — she became the campaign. She and Meryl Streep appeared together on the cover of Vogue, a moment that collapsed the distance between reality and fiction in a way that felt genuinely surreal. The two women — one who inspired a character, one who immortalized it — photographed side by side as if the last 20 years of careful deflection had simply never happened.
The pair also filmed a YouTube skit together as part of the promotional rollout. Wintour made a deal with the Devil, as one outlet put it — but the more interesting question is why she chose to, and why now.
The answer has several layers. Wintour stepped down as Vogue's editor-in-chief in June 2025 after 37 years in the role, transitioning to global editorial director. That change in title represents a meaningful shift in her relationship to institutional power — she no longer runs the magazine on a daily basis, and with that separation comes a certain freedom. She doesn't have to be Miranda Priestly anymore, because she's no longer in the chair Miranda Priestly occupied.
There's also the uncomfortable reality that the sequel's premise mirrors Vogue's actual situation. The magazine announced in 2025 that it would cut its print run to just eight issues a year. U.S. Vogue's paid digital subscribers currently number around 153,075 — roughly one-eighth of the 1.2 million print copies per issue the magazine sold in 2006. When the movie's villain is watching her empire crumble under the pressure of the digital age, Wintour engaging with that story isn't just savvy PR — it's a form of acknowledgment that the world the original film satirized has genuinely changed.
Madonna, Wintour, and the Confessions II Theatrical Promo
If the Vogue cover was surprising, the Madonna collaboration is genuinely unprecedented. Billboard reported on May 2 that a 30-second theatrical teaser for Madonna's upcoming album Confessions II is screening in cinemas ahead of showings of The Devil Wears Prada 2 — and it features Wintour and Madonna together.
The footage appears to be drawn from the Dolce & Gabbana Women's Fall/Winter 2026 Fashion Show in Milan on February 28, 2026, where the two were photographed sitting together in the front row. That a front-row fashion show appearance has been repurposed into a theatrical album teaser is the kind of cross-promotional creative thinking that would have seemed like parody five years ago.
Confessions II, due July 3, is a follow-up to Madonna's seminal 2005 album Confessions on a Dance Floor. The lead single, 'Bring Your Love,' features Sabrina Carpenter and premiered at Coachella's second weekend on April 17, 2026. The entire campaign — Carpenter, Wintour, the Devil Wears Prada 2 tie-in — positions Confessions II as an event, not just a record release.
For Wintour, the Madonna association is meaningful in a different way. These are two women who have shaped culture for four decades, who have occasionally orbited each other in the fashion and entertainment worlds, and who are now, in their later chapters, making the most visible use of that connection. It reads less like a promotional stunt than a statement: we're still here, we're still relevant, and we're doing it our way.
The Original Sin: Lauren Weisberger, the Book That Started It All
To understand why this moment matters, you have to go back to 1999, when a young woman named Lauren Weisberger spent 10 months as Wintour's assistant at Vogue. The experience apparently left a mark. In 2003, Weisberger published The Devil Wears Prada, a roman à clef that thinly fictionalized her time working for fashion's most formidable gatekeeper. The book sold 13 million copies worldwide.
The novel's success, and then the film's, created a paradox for Wintour: the more she denied the connection, the more the denial itself confirmed it. Miranda Priestly — fur-coated, soft-voiced, casually devastating — became the public's mental image of Wintour whether Wintour liked it or not. The question of whether Streep's portrayal was accurate became less relevant than the fact that it had become definitive.
That Wintour has now embraced Streep enough to appear on a Vogue cover with her suggests one of two things: either the distance of time has genuinely softened the sting, or Wintour has calculated that owning the narrative is more powerful than resisting it. Given her history, the second explanation seems more likely.
The Meghan Markle Dimension
Wintour's cultural footprint isn't limited to the sequel's promotional blitz. Reports surfaced around May 1, 2026, that Meghan Markle has been snubbed from the Met Gala amid an ongoing rift with Wintour — one of several high-profile relationships the Duchess of Sussex is reportedly navigating badly.
The roots of that conflict reportedly trace back to 2019, when Markle collaborated with British Vogue editor Edward Enninful on a guest-edited issue rather than working with Wintour's U.S. Vogue. In a world where Wintour controlled access to the fashion establishment, that choice was widely interpreted as a slight — and one that apparently has lasting consequences. The Met Gala, which Wintour has chaired since 1995, remains one of the most powerful gatekeeping mechanisms in celebrity culture.
The timing of the Markle reports — landing on the same day The Devil Wears Prada 2 opened — is either coincidental or a reminder that Wintour's influence, even in a post-editorship role, continues to shape who gets in and who doesn't.
What This Means: Power, Legacy, and the Reinvention of a Villain
The Anna Wintour moment of spring 2026 is more than just a press cycle. It's a case study in how cultural power evolves — and how smart operators manage the transition from institutional authority to something more diffuse and harder to define.
Wintour built her power through scarcity: access to Vogue was currency, and she controlled the mint. The digital disruption that hollowed out print media didn't just shrink the magazine — it eroded the fundamental logic of that power structure. When anyone can publish, when Instagram made every stylist a taste-maker, the editor-in-chief of Vogue became less of an absolute monarch and more of a respected voice among many.
Her response to that shift has been, characteristically, to play offense. Stepping down from the editor role before being pushed, transitioning to a global advisory position that isn't tied to a single masthead, and then embracing the film that once seemed to mock her — these are the moves of someone who understands that the best way to protect a legacy is to get ahead of it.
The Devil Wears Prada 2 storyline about Runway facing financial ruin and a potential sale to an oligarch isn't just fiction with a convenient real-world parallel. It's a mirror that Wintour is holding up, voluntarily, because the reflection is more flattering now than it was in 2006. Then, she was the villain. Now, the real villain is the economic force dismantling everything the villain built — and by stepping into the frame, Wintour becomes something more sympathetic: the keeper of a tradition that may not survive.
The clearest sign of Wintour's savviness: she didn't just endorse the sequel — she made it impossible to tell where the movie ends and her actual life begins. That blurring of lines is not accidental. It's the most powerful kind of branding.
Frequently Asked Questions
Is Anna Wintour actually in The Devil Wears Prada 2?
Wintour does not appear in the film itself, but she has been central to its promotional campaign. She appeared with Meryl Streep on the cover of Vogue and in a YouTube promotional skit. She also appears alongside Madonna in a 30-second theatrical teaser for Confessions II that screens before showings of the film — footage drawn from their front-row appearance at the Dolce & Gabbana Fall/Winter 2026 show in Milan.
Why did Anna Wintour step down from Vogue?
Wintour stepped down as editor-in-chief of Vogue in June 2025 after 37 years in the role. She transitioned to the position of global editorial director, a title that gives her oversight across Condé Nast's international Vogue properties without the day-to-day responsibilities of running a single masthead. The move came as Vogue announced it would reduce its print frequency to eight issues per year, a significant contraction from its historic output.
What is the plot of The Devil Wears Prada 2?
The sequel centers on Runway magazine — the fictional fashion publication from the original film — facing the kind of existential crisis that has consumed real print media. The story involves potential layoffs and the possibility of selling the magazine to an oligarch. Meryl Streep, Anne Hathaway, Emily Blunt, and Stanley Tucci all return to their original roles. The premise directly mirrors real-world challenges facing legacy fashion publications like Vogue.
What happened between Meghan Markle and Anna Wintour?
The reported rift stems from 2019, when Meghan Markle collaborated with British Vogue editor Edward Enninful on a guest-edited issue rather than partnering with Wintour's U.S. Vogue. In Wintour's world, that choice was read as a deliberate slight. The consequences have reportedly been long-lasting: Markle has been snubbed from the Met Gala, which Wintour controls as its longtime chair.
What is Madonna's Confessions II, and what does it have to do with Anna Wintour?
Confessions II is Madonna's forthcoming album, due July 3, 2026. It follows up her landmark 2005 dance record Confessions on a Dance Floor. The lead single 'Bring Your Love,' featuring Sabrina Carpenter, debuted at Coachella in April 2026. A theatrical teaser for the album, featuring both Madonna and Wintour, screens before showings of The Devil Wears Prada 2 — a cross-promotional arrangement that ties together three of the biggest entertainment stories of spring 2026.
The Bottom Line
Anna Wintour has spent her career controlling access and narrative. The spring 2026 campaign — the Vogue cover with Streep, the Madonna promo, the theatrical tie-in — represents a masterclass in the same skill applied to her own mythology. By embracing the story that once threatened her, she has made herself central to one of the biggest entertainment moments of the year while quietly reframing what that story means.
The decline of print that the sequel depicts is real. Vogue's circulation numbers tell a stark story. But the cultural authority that Wintour accumulated across nearly four decades isn't stored in print pages — it lives in relationships, in access, in the institutional memory of who got in and who didn't. That kind of power doesn't disappear when the masthead changes. It just changes form.
Whether The Devil Wears Prada 2 turns out to be a worthy sequel is a separate question. What's not in question is that Wintour has turned its release into something that extends well beyond film criticism — a renegotiation, in public, of her own legacy. The Devil, it turns out, needed no deal. She was always in control.
