Anna Wintour: a rare face-to-face with the most important woman in fashion

The editor-in-chief of American Vogue talks to Jess Cartner-Morley about Michelle Obama, fake news and only spending 20 minutes at parties.

Portraits by Tyler Mitchell

• Read more from the spring/summer 2019 edition of The Fashion, our biannual fashion supplement

One morning last August, Anna Wintour was playing tennis with her coach in the 40-acre grounds of her Long Island summerhouse. She noticed he seemed a little distracted: “But his wife was about to have a baby, so I thought he was nervous about that.” Then it struck her that they had attracted an unusual number of spectators. The house was brimful with family, but it was earlier than most people get up on a weekend. (“I’m a morning person,” says Wintour, for whom anything later than 5am constitutes a lie-in.) As she prepared to serve, she heard a car pull up. “I am pretty OCD about guests and where they are sleeping. I thought, I’m not expecting anyone else, I don’t have any more rooms. Who is this? And then I thought – that looks like Roger [Federer, with whom Wintour is good friends]. And that looks like [his wife] Mirka. And that looks like their twins.” Wintour’s daughter Bee Shaffer, it transpired, had arranged for a Federer-Wintour family tennis tournament, “which was the best gift a daughter could give a tennis-mad mother. I got to play doubles with Roger for the first time in our very long friendship, against my two nephews.” Twenty-five floors above Manhattan, behind the ebonised mahogany Alan Buchsbaum desk from which she has ruled the fashion world for three decades, she leans back in her chair and smiles at the memory. “We won, of course.”