Anna Wintour Bonds With Meryl Streep at Milan Fashion Week 2025

Meryl Streep made a surprise appearance at Milan Fashion Week 2025, where she crossed paths with legendary magazine editor Anna Wintour.

“How are you?” Wintour, 75, asked Streep, 76, in a Saturday, September 27, Instagram video shared by Vogue, as the two women exchanged a hug. “I can’t believe you flew from New York to Milan.”

While Wintour opted for a floral gown with her signature sunglasses, Streep donned a camel-colored Dolce & Gabbana trench coat cinched with a leopard-print belt to match her handbag. The legendary actress accessorized her look with nude slingback pumps, sunglasses of her own and jewelry from Vhernier.

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

Streep was joined by her Devil Wears Prada 2 costars Stanley Tucci and Simone Ashley, who also wore D&G ensembles for the brand’s MFW presentation. The crew sat beside supermodel Naomi Campbell, according to images shared by Vogue.

Streep famously starred in 2006’s The Devil Wears Prada, portraying Miranda Priestly, the iconic editor-in-chief of the fictional Runway magazine. The character was heavily rumored to be inspired by Wintour, who stepped down from her position at Vogue earlier this year. (Wintour will continue to serve as the publication’s global editor and the global chief content officer for parent company Condé Nast.)

“It had a lot of humor to it. It had a lot of wit to it,” Wintour said on The New Yorker’s “Radio Hour” show earlier this month, discussing the movie. “It had Meryl Streep. I mean, it [had] Emily Blunt. They were all amazing. In the end, I thought it was a fair shot.”

In The Devil Wears Prada, Streep’s Miranda rules Runway with an iron fist (or should we say stiletto?) with the help of assistants Emily and newcomer Andy, played by Blunt, 42, and Anne Hathaway, respectively. It’s never been officially confirmed whether Miranda was based on Wintour personally.

“Well, I went to the premiere wearing Prada completely having no idea what the film was going to be about,” Wintour recalled to the outlet. “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!”

As for Streep, she’s recently been hard at work filming the highly anticipated sequel to The Devil Wears Prada with Blunt, Tucci, 64, and Hathaway, 42, 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 told Women’s Wear Daily in 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.