Seeing Double: Fashion’s Most Influential Bosses Unite in Vogue’s May 2026 Issue
Seeing Double: Fashion’s Most Influential Bosses Unite in Vogue’s May 2026 Issue
By Sophie Amen - April 23, 2026
The cover of Vogue’s May 2026 issue is feeding both fashion and film fans alike. It captures The Devil Wears Prada’s Meryl Streep and Vogue’s Anna Wintour—both dripping in Prada, of course. It brilliantly showcases their unique relationship and the power they hold in the world of pop culture.
Since the announcement of The Devil Wears Prada 2—premiering May 1—fans have been on the edge of their seats. It’s telling that two decades after the release of The Devil Wears Prada, the film and its characters still resonate with audiences, and at the center of it all is Miranda Priestley. Streep will return in the sequel to portray the formidable editor-in-chief of Runway Magazine. As excitement continues to build around The Devil Wears Prada 2, it would be impossible to ignore Wintour, the magazine mogul long-rumored to be Priestly’s real-life counterpart.
While it’s never been explicitly confirmed or denied, audiences in 2006 quickly noticed Priestly’s correlations to Wintour, Vogue’s former editor-in-chief who shaped the magazine into a global fashion authority. The unwavering gaze, the oversized sunglasses, and the quiet authority were only a few details that made Priestly feel a little less fictional.
For the May issue, Streep and Wintour sat down for a conversation with director Greta Gerwig to answer a fascinating question: What happens when you put two Miranda Priestlys in a room? Combined with a remarkable shoot by photographer Annie Leibovitz, the conversation covered everything from power to fashion to acting the part.
“I’d like to say it’s such an honor to be played by Meryl, however distant Miranda is from myself,” Wintour said. “Who wouldn’t think that that wasn’t the most extraordinary gift?”
Priestly and Wintour certainly have their similarities, similarities that might be too specific to be a coincidence. As the sequel’s release date quickly approaches, one can’t help but note how the cultural landscape surrounding the movie and the characters has shifted since the original in 2006.
“Today fashion is so much more democratic, and its influence is enormous. It’s central to the culture,” Wintour said on the topic of how fashion used to be thought of as elitist.
The sequel, while offering the opportunity to revisit beloved characters, also presents a new possibility: the cost of staying powerful in an industry that never stops changing. The once rigid boundaries of fashion have softened, so many question if Priestly’s brand of authority still exists. What will the character look like in 2026?
“In terms of Miranda, and coming back to that character 20 years later, 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,” Streep said on building the 2026 version of Priestly.
So, get ready to reenter the cutthroat world of Runway Magazine and find out what Priestly has been up to for the past 20 years. With Streep's attention to detail and the ever-evolving world of fashion, we can’t wait to see what the sequel has to offer.
For more fashion, beauty, and lifestyle content, keep reading Square Magazine. Follow Square on Instagram for exclusive content.
All images belong to their respective owners.