Meryl Streep meets Anna Wintour at Milan Fashion Week: A real life ‘Devil Wears Prada’ moment

Milan Fashion Week witnessed a surreal crossover on September 27, when Hollywood fiction collided with fashion reality. Meryl Streep, dressed as her iconic character Miranda Priestly from The Devil Wears Prada (2006), came face-to-face with Vogue’s legendary editor Anna Wintour, the woman long believed to have inspired Priestly.

The encounter happened backstage at Dolce & Gabbana’s Spring 2026 runway show, where both women- unsurprisingly- wore their signature oversized sunglasses. Vogue shared a now-viral Instagram video capturing the moment. In the clip, Streep greets Wintour warmly, joking, “This is my first fashion show,” while stepping out of Priestly’s famously icy persona.

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Joining Streep was Stanley Tucci, reprising his beloved role as Nigel Kipling, alongside Bridgerton star Simone Ashley, who will appear in The Devil Wears Prada 2. The actors, seated in the front row, dressed head-to-toe with Dolce & Gabbana, were also filming scenes for the highly anticipated sequel.

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A viral full-circle fashion moment

For fans, the sight of Miranda Priestly meeting Anna Wintour was nothing short of cinematic. Wintour, who helmed Vogue from 1988 until 2025, has long been seen as the real-life counterpart to Priestly- the impeccably dressed, sharp-tongued editor of Runway magazine in the movie.

The Dolce & Gabbana press office later confirmed that filming for The Devil Wears Prada 2 was underway at the Milan event. Throughout the show, Streep and Tucci stayed in character, studying the runway with the same intensity that made their roles unforgettable nearly two decades ago.

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What to expect from The Devil Wears Prada 2

The sequel, slated for release in May 2026, will reunite much of the original cast. Alongside Streep and Tucci, Anne Hathaway returns as Andy Sachs, while Emily Blunt reprises her role as the ambitious Emily Charlton, now reimagined as a powerful advertising executive.

Other returning cast members include Tibor Feldman and Tracie Thoms, while newcomers Lucy Liu, Justin Theroux, Pauline Chalamet, and B.J. Novak join the team. David Frankel once again directs, with Aline Brosh McKenna handling the screenplay.

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This new chapter will explore Runway magazine’s struggle in the digital era, reflecting the real-world decline of print media, a timely evolution for the story that once satirized the cutthroat fashion publishing world.

Anna Wintour on the film’s legacy

Interestingly, Wintour herself has previously addressed her thoughts on the original film. Speaking on The New Yorker Radio Hour, she admitted she found the movie “very funny,” especially with Streep in the lead. “Miuccia [Prada] and I talk about it a lot,” she revealed, “and I say to her, ‘Well, it was really good for you.’”

The Devil Wears Prada 2 will hit theatres in May 2026.