Meryl Streep made an unexpected appearance at Milan Fashion Week 2025 on Saturday, September 27, surprising legendary Vogue editor Anna Wintour. The pair met in Milan, marking a notable moment during the high-profile fashion event as Streep embraced the occasion with her signature style. This surprising occurrence has attracted significant attention, especially given the connection between Streep’s famous film character and Wintour’s real-life persona.
Fashion Choices Reflect Iconic Style
At the event, Anna Wintour appeared in one of her trademark ensembles, choosing a floral gown paired with her signature sunglasses. In contrast, Streep showcased a sophisticated look with a camel-colored Dolce & Gabbana trench coat, accented by a leopard-print belt and matching handbag. She completed her outfit with nude slingback pumps and sunglasses, blending elegance with understated fashion statements.
Streep’s First Fashion Show Experience
During their brief encounter, Wintour greeted Streep warmly via an Instagram video shared by Vogue, asking, “How are you?” as the two embraced. Streep revealed with a playful tone,
“This is my first fashion show. Not kidding. My first.”
Wintour expressed amazement, saying,
“I can’t believe you flew from New York to Milan,”
highlighting the rarity of the actress’s presence at such events.
Support from Co-stars and Industry Icons
Joining Streep at the Dolce & Gabbana show were her “Devil Wears Prada” co-stars Stanley Tucci and Simone Ashley, who also wore Dolce & Gabbana ensembles during the Milan Fashion Week presentation. The group was seated next to supermodel Naomi Campbell, adding further star power to the occasion according to images released by Vogue. The gathering underlines the strong ties between the film’s cast and the fashion world.
The Legacy of “The Devil Wears Prada” and Its Connection to Wintour
Streep’s role as Miranda Priestly in the 2006 film “The Devil Wears Prada” remains iconic, portraying the demanding editor-in-chief of the fictional Runway magazine. The character has long been rumored to be inspired by Anna Wintour, who recently stepped down as Vogue’s editor-in-chief but continues as the global editor and chief content officer of Condé Nast. Wintour has openly reflected on the movie’s portrayal of the fashion industry and her perceived image within it.
On The New Yorker’s Radio Hour earlier this month, Wintour remarked on the film’s tone, saying,
“It had a lot of humor to it. It had a lot of wit to it.”
She praised the cast, noting,
“It had Meryl Streep. I mean, it [had] Emily Blunt. They were all amazing. In the end, I thought it was a fair shot.”
Wintour’s Perspective on the Film’s Impact
Wintour also recalled her initial experience with the film’s premiere:
“Well, I went to the premiere wearing Prada completely having no idea what the film was going to be about,”
she said. She noted concerns within the fashion industry over how the film might depict her image, explaining,
“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.”
On her conversations with Prada designer Miuccia Prada, Wintour shared with a hint of humor,
“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!”
Ongoing Work on The Devil Wears Prada Sequel
Meanwhile, Streep remains actively engaged in filming the highly anticipated sequel to “The Devil Wears Prada” alongside Emily Blunt, Stanley Tucci, and Anne Hathaway in New York City. Hathaway recently expressed excitement about returning to her role, telling Women’s Wear Daily in December 2024,
“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.”
She added with enthusiasm,
“I cannot tell you a thing!”
It remains unclear whether Streep, Tucci, and Simone Ashley’s presence at Milan Fashion Week was related to filming scenes involving Anna Wintour or simply part of attending the fashion show.
The Significance of This Meeting at Milan Fashion Week
The encounter between Meryl Streep and Anna Wintour at Milan Fashion Week represents more than a brief reunion; it highlights the continuing cultural impact of a film that bridged fashion and cinema. With Streep stepping into a fashion environment for the first time, her presence alongside industry leaders signals a blurring of boundaries between entertainment and style. As the sequel to “The Devil Wears Prada” progresses, fans and insiders alike are watching closely to see how these worlds will continue to intersect.
