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.