Anna Wintour Stunned by Meryl Streep’s Milan Fashion Week Trip

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Meryl Streep Makes Surprise Appearance at Milan Fashion Week 2025

Meryl Streep made a surprising appearance at Milan Fashion Week 2025, where she crossed paths with the legendary magazine editor Anna Wintour. The encounter was captured in an Instagram video shared byVogue, showing the two women exchanging a warm hug and engaging in a brief conversation.

“How are you?” Wintour, 75, asked Streep, 76, in the video. “I can’t believe you flew from New York to Milan.”

Wintour was seen wearing a floral gown paired with her signature sunglasses, while Streep opted for a camel-colored Dolce & Gabbana trench coat cinched with a leopard-print belt that matched her handbag. She completed her look with nude slingback pumps, her own sunglasses, and jewelry from Vhernier.

“This is my first fashion show,” Streep playfully told Wintour. “Not kidding. My first.”

A Star-Studded Gathering

Streep was joined by herDevil Wears Pradacostars Stanley Tucci and Simone Ashley, who also wore D&G ensembles for the brand’s MFW presentation. According to images shared byVogue, the group sat beside supermodel Naomi Campbell.

Streep famously portrayed Miranda Priestly, the iconic editor-in-chief of the fictionalRunwaymagazine, in the 2006 filmThe Devil Wears Prada. The character was heavily rumored to be inspired by Wintour, who stepped down from her position atVogueearlier this year. However, Wintour will continue to serve as the publication’s global editor and the global chief content officer for parent company Condé Nast.

Reflections on the Original Film

In a recent interview onThe New Yorker‘s “Radio Hour” show, Wintour reflected on the movie. “It had a lot of humor to it. It had a lot of wit to it,” she said. “It had Meryl Streep. I mean, it had Emily Blunt. They were all amazing. In the end, I thought it was a fair shot.”

InThe Devil Wears Prada, Streep’s Miranda rulesRunwaywith an iron fist, aided by assistants Emily and newcomer Andy, played by Blunt and Anne Hathaway, respectively. While it has never been officially confirmed whether Miranda was based on Wintour personally, the connection has long been speculated.

A Fun Conversation About the Film

Wintour shared some amusing memories about the film. “Well, I went to the premiere wearing Prada completely having no idea what the film was going to be about,” she recalled. “I think that the fashion industry [was] very sweetly concerned for me about the film, that it was going to paint me in some kind of difficult light … [like] a caricature. But, first of all, it was Meryl Streep, which [was] fantastic. Then, I went to see the film and I found it highly enjoyable and very funny.”

She added, “Miuccia [Prada], the designer, and I talk about it a lot. I say to her, ‘I was really good for you.’ And you can imagine what she says back!”

Preparing for the Sequel

As for Streep, she’s currently hard at work filming the highly anticipated sequel toThe Devil Wears Pradawith Blunt, Tucci, and Hathaway across New York City.

“I’m so excited that now I can do that for other people, that now I have the knowledge and the experience and the confidence to take care of other people on sets in which I’m looked at as a leader,” Hathaway toldWomen’s Wear Dailyin December 2024 of her return to the role. “I cannot tell you a thing!”

The Associated Press later confirmed that Streep, Tucci, and Ashley were filming a scene for the sequel at the fashion show. The sequel is expected to bring back the beloved characters and explore new stories within the world of high fashion.

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Passionate writer for MathHotels.com, committed to guiding travelers with smart tips for exploring destinations worldwide.

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