I impatiently waited for Anna to enter the Minetta Tavern, one of Wintour’s favorite restaurants, located in Greenwich Village, just a block from her home. (Before Minetta was Wintour’s go-to steakhouse, it was home to some of the most popular writers from the Beat Generation like Jack Kerouac and William Burroughs!) Finally, Anna walked in and she looked exactly how I had imagined, prim and proper, elegant and sophisticated, and of course only cracking her classic “no-teeth” smile. She wore a floral print dress and rocked her ever-timeless bob of course. I stood from my table to greet her and make her comfortable to sit with me, as we would be spending the next hour or so together. Anna ordered a steak and I ordered a salad, and we jumped right in!
“We can just start with the basics, where were you born and raised and when?
Anna Wintour: “ I was born on November the third in 1949, in the city of London.”
Me: “Can you explain to me how you got your start?”
AW: “My father, Charles, was the editor of The London Evening Standard newspaper, so very much of my inspiration to be an editor came from him certainly. Although my father and I did not have the closest of bonds, I truly did learn quite a lot from him and owe much of my success to him.”
“What made you decide to drop out of your finishing school when you were so young?”
AW: “I truly did not believe the world of academia was the world for me, as it is not for everybody. I do not think I would be where I am right now if I had continued on that path.”
“How did you get into the fashion industry?”
AW: “Fashion more or less landed in my lap. I was always quite certain of myself and dressed myself and friends from a very young age, I did not take well to uniforms that were enforced at finishing school. Dress is meant to be unique and I saw a great deal of inspiration in that.”
“When exactly did you cut your hair into the iconic bob you possess today?’
AW: “I believe I made that choice at around 15 years of age and as you notice, it has changed very little in the past 51 years.”
“How would you describe your relationship with fashion and clothing? How has that developed over time?”
AW: I began my career at Harper’s and Queen in London, which is now known as Harper’s Bazaar of course. It has certainly evolved since changing positions and becoming the editor in chief at Vogue. I have much more knowledge and exposure to fashion, obviously.
“When you are not ruling the fashion world, what is your favorite pass time?”
AW: “Most definitely tennis. I often wake up at 5 am just to get a round of tennis in before my day begins. I’ve attended the US Open, Wimbeldon Championships, and French Open Tournaments, I just adore the sport.”