The Superpowers of Anna Wintour

THE WORKSHOP: A Conversation about Failing Upward, Decisiveness, Alliances, Fashion, and Ambition

As most people who know me well will say, I am not terribly interested in fashion. My color palette borders on monochrome, and I buy for longevity rather than the latest trends.

But I am fascinated by Anna Wintour, editor-in-chief of Vogue. Her fearsome reputation. Her look. Her iconic command of fashion and media. Her longevity. That’s why I’m so glad to open my new series, THE WORKSHOP, with Wintour’s biographer Amy Odell. In this series, I’ll interview authors and other experts to draw out lessons on success, happiness, creativity, motivation, and general ‘work-life’ achievement.

A fashion journalist, Odell spent years interviewing Anna Wintour’s friends and associates. Her biography ANNA has earned critical (and bestselling) acclaim for its incisive, revealing profile of this cultural giant. The chronicle of Wintour’s rise to the top of Vogue provides many lessons. Her ability to maintain that position for decades—and grow her influence—provides still more. 

This is my conversation with Amy, condensed and edited to avoid my incessant interruptions…No conversation can match reading the book. I recommend it highly. Also, Amy has her own fashion Substack, BackRow, which is wonderful.

Who is Anna Wintour? In my world, fashion, this is impossible not to know. But the first time I met my mother-in-law, and I brought up Anna, she said, “Who’s that?” I was stunned. How I would explain it today would be that Anna is the editor-in-chief of Vogue, who is most famous for the Meryl Streep depiction in The Devil Wears Prada.

I find that the work people choose to do is often channeled by their families. Tell me about Anna’s… Her father was a famous newspaper editor of the Evening Standard in London. He was very well respected. It was the place where a young, talented journalist on Fleet Street wanted to work. People really admired him. His background was as a political editor and reporter, but he took culture seriously. From a young age, Anna had exposure to a glamorous and intellectual sort of world. Her parents would throw dinner parties with journalists, artists, politicians, and other influential people, and Anna was at the table.

Her mother came from money on the East Coast. She was interested in journalism and did some writing. But after she had kids, she turned to social work, particularly helping pregnant teens. She devoted herself to this work. In reporting on Anna, I was surprised to learn she wants her legacy to be her philanthropy more than anything she did as an editor. I suspect that comes from her mother.

How did her interest in fashion develop?