Anna Wintour Only Packed One Shoe Trend for Milan FW

Even though she’s passed the Vogue U.S. baton to Chloe Malle, Anna Wintour retains her perch at the top of the fashion industry. She’s still the global editorial director of Vogue and the global chief content officer of Condé Nast, so she has plenty of people to manage, deadlines to meet, and advertisers to court. Her outfits, however, are one thing she doesn’t have to worry about. Why? Because she relies on a tried-and-true uniform that she never wavers from. In the winter, her formula consists of a long coat, a printed dress, and tall snakeskin boots. Oh, and her precisely sheared bob haircut and oversize black sunglasses, of course.

During the fall 2026 runway season in London and Milan, Wintour has been changing her coats and dresses to attend different shows, but hasn’t strayed from her favorite snake-print heeled boots, of which she owns a few variations. I’m sure she has every shoe designer in the world at her beck and call, but she’s not willing to ditch her reliable boots. If it’s not broken, why fix it? Scroll down to see a few examples of how she’s styled the snake-print boots with different outfits this fashion month so far.