Meryl Streep and Anna Wintour Face Off (Again!) at Milan Fashion Week for ‘Devil Wears Prada 2’
MILAN, ITALY – In a moment that blurred the lines between high fashion fantasy and cinematic reality, two titans of style converged at Milan Fashion Week. On Saturday, September 27, legendary actress Meryl Streep, 76, embodying her iconic role as the formidable fashion editor Miranda Priestly, came face-to-face with the woman who famously inspired the character: Anna Wintour, 75, the long-reigning editor-in-chief of American Vogue. The highly anticipated encounter, captured in a viral video shared by Vogue on Instagram, sent ripples of excitement through the fashion world and Hollywood alike.
The setting was the prestigious Dolce & Gabbana Spring/Summer 2026 show, a highlight of Milan Fashion Week. Streep, fully immersed in Priestly’s chillingly chic persona, commanded attention from the front row. Dressed in a striking latex camel-colored trench coat, cinched with a leopard print belt and complemented by a matching clutch, black pants, pristine white sunglasses, and elegant satin pumps, her character’s signature white-gray cropped hairstyle was perfectly in place. Beside her sat Stanley Tucci, 64, reprising his beloved role as Runway magazine’s art director, Nigel Kipling, equally in character.
Across the runway, a mere few feet away, sat Anna Wintour. Known for her impeccable style and stoic demeanor, Wintour, in a colorful floral print maxi dress paired with snakeskin heeled boots and accessorized with gold chain necklaces and her trademark black sunglasses, observed the show. Behind the fictional duo, costar Simone Ashley, 30, also joined the entourage, set to introduce a new character in the sequel.
But it was the pre-show interaction that truly captivated. Before taking their seats, Streep and Wintour met, sharing a warm hug and engaging in a seemingly pleasant chat amidst a lavish leopard print interior. For fans of the 2006 blockbuster The Devil Wears Prada, based on Lauren Weisberger’s novel, seeing the fictional editor and her real-life muse share such a moment was nothing short of surreal. The original film, a cultural phenomenon, grossed over $326 million worldwide and cemented Miranda Priestly as one of cinema’s most memorable antagonists, a character heavily rumored to be inspired by Wintour’s formidable reputation at Vogue.
This Milan sighting is part of ongoing production for The Devil Wears Prada 2, a sequel nearly two decades in the making. Filming has been underway for several months, with Streep having been spotted in August 2025 in New York City, dazzling in a dramatic red ballgown while shooting a Met Gala-esque scene at the American Museum of Natural History. That sequence also featured Tucci, alongside other unconfirmed cast members, hinting at the grand scale of the follow-up.
The sequel promises to delve deeper into the high-stakes world of fashion publishing. According to Variety, the narrative will follow Priestly as she navigates the turbulent waters of a declining traditional magazine industry, facing new challenges and a potential rivalry with Emily Blunt’s character, Emily Charlton. Charlton, last seen as Priestly’s senior personal assistant, has reportedly ascended to a high-powered executive role within a luxury group, controlling crucial advertising budgets that Priestly desperately needs. Anne Hathaway is also confirmed to return as Andrea “Andy” Sachs, completing the central trio.
With filming progressing in both Milan and New York, the anticipation for The Devil Wears Prada 2 is reaching a fever pitch. Fans eager to witness the return of fashion’s most iconic boss, and the continued intertwining of fictional glamour with real-world influence, can mark their calendars for the film’s scheduled release on May 1, 2026.
