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.
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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? Anna grew up in London in the 1960s. It’s a time when everything in the world just points there. You have the Beatles; you have Vidal Sassoon and Bob haircuts; you have Mary Quant and miniskirts. Anna credited her interest in fashion to that time and place when she came of age. In her house, they talked about these trends. And, Anna had resources, she was able to buy and enjoy fashion personally. Fashion is about the luxury industry, and who really has access to that, but the wealthy.
Did fashion—or rather her interest in it—become her identity? In a way, Anna’s much more complex than that. She always demonstrated a strong interest in culture. And power. If you think of the time, the late 1960s through the 80s, when Anna rose up, that was a very different period for women.
Meaning not every industry was available to them? I can’t say if she thought about it in these terms, but fashion was a way for Anna to ascend.
Was being Charles Wintour’s daughter helpful to her career? The editor at Harper’s & Queen, where Anna got her first job at a fashion magazine, told me that he suspected Anna would be good because she was Charles’s daughter.
Not to get ahead of myself, but she seems to have taken that lesson, about connections, and applied it through the rest of her life, being a nexus? I hadn’t thought about that before, but yes, yes, absolutely.
Her early career progression serves as a kind of masterclass in failing upward. After four years and some internal infighting, she quits Harper’s & Queen. She moves to New York and takes a job as a junior fashion editor at Harper’s Bazaar. Not a year later she is fired. What’s happening? Well, she was young and edgy. She wanted to do what she wanted to do. That’s kind of her way, and it didn’t work out. We see all the time where people who are not that talented do very well in a stuffy corporate environment, and people who are talented get fired. So, I think that’s what she had to work out early on: the politics. And to her credit, she did learn how to get people to come around to her point of view.
Bob Guccione, the Penthouse publisher, hires her at his magazine Viva to be fashion editor. That goes belly up. The upside at Viva was she had a lot of freedom, and you start to see in her spreads and the magazine the kind of work that she went on to do with Vogue.
After Viva, she gets a job at Savvy, a career woman’s magazine. That doesn’t work out. But again, she climbs higher, becoming fashion editor at New York magazine. That’s the job that really changes things for her. It makes her a star.
She excels at New York, innovating and making a splash. But let’s take a step back, where does she get this ability, even at a young age, to be so bold and uncompromising? It’s kind of that nature versus nurture question. But she’s always been described as quite confident in what she’s doing. And this is interesting, because she’s also described as shy, and this is what makes her kind of a complicated, tricky person to write about. There are all these diametric aspects of her personality.
Her goal was always to run Vogue though, right? It’s a very lofty goal to be the editor-in-chief of the number one, most influential fashion magazine in the world? Yes, that ambition was in her heart since her early 20s, perhaps earlier. There’s a story about how she was filling out a form about her career ambitions, and she asked her dad what she should put in, and he said, ‘Editor-in-chief of Vogue’. And she never looked back from that.
The power of high ambitions. Let’s dive into how she was so innovative. What was it about her spreads at New York that made her a star? For a long time in fashion shoots, there was a model in a garden with soft makeup and soft hair and a nice dress. The signature Anna developed was blending culture with fashion, so her spreads were like mixing a taxi driver into a shoot with a model. Or incorporating art into her backgrounds.
I love this quote in your book about cultural immersion as a significant factor in her craft. “Developing a creative eye is something that you have within you, but something that you can develop through exposure to culture to the arts, through reading, visiting museums, looking at what’s going on in the world around you.” Anna made it a point to see everything. In the early 80s, the downtown art scene was such a big deal.
Then she gets the big job at Vogue and doubles down on this in a way? If you look at old Vogue spreads, they might just be like dresses or jackets on a model. The shape of the clothes was what obsessed her predecessor, Grace Mirabella. Anna was thinking about fashion in a really different way, which was culture and context and why now versus why this thing. And then you see celebrities come in. Because if you look at culture, they’re becoming more important. You begin to see actresses on covers.
So, she took fashion out of its own silo? She brought culture and fashion together in a beautiful way that people admired.
I’d like to venture into what I call, Anna’s superpowers, the characteristics that made her successful. First, is her work ethic. From your biography, I understand she gets up at 4:30 a.m. and keeps going until 11 pm at night, reviewing the dummy copy of the magazine until bedtime. When I was writing the book, I was so pregnant, up late, up early, sleeping four hours a night. And I would say to my husband ‘I can’t keep doing this and then I’d reflect, what would Anna do. Because she did. She would get it done whatever it takes. Those 8–10-page fashion spreads she would do with artists. You must convince 8-10 artists to do it. It’s hard to get people to do things. They were very work intensive, but she worked hard, and she executed them well.
But working hard is not enough, right? What other qualities made her good? Above all, really, to stay at the top and a company like Conde Nast for that long. It's corporate politics. There are many talented editors who could put out a beautiful version of Vogue, there just are. She's good at it, but she’s also been very savvy for a very long time about forming alliances with people who she needs. You need certain people to have your back in a big corporate environment. She made sure that she had that. And for most of her tenure, it's a lot of men at the top, and she really disarmed them. They didn't really know what to do with her.
What other superpowers? She's not gossipy. She doesn't get bogged down in things. This plays very well in a corporate environment. She tries to keep moving and get things done that need to get done and not let it frustrate her if there are problems. If they did a story, and it didn't work, she would just say, you know, not every idea works, and they would move on. She wouldn't berate them or complain about it. That’s important to understand.
Another thing that stands out to me about Anna: She's not flaky at all. That sounds like a small thing, but it's a big deal. The things that need a response, she will get back to people because she feels that that's the right thing to do. You know, like to not keep people waiting to just reply to the email, get it over with so she can move on. And so that person can move on.
And her decisiveness? She makes decisions fast, and she moves on. She almost never changes her mind. People know if she says something, that’s it. She commands respect rather than demands it.
Following up on that, what is it about her presence, the way she walks into a room? Her presence can be intimidating. It sounds cheesy, but that is the power of fashion. People will admit that when they look their best, they feel their best. With Anna, she basically wears a uniform. It’s a printed dress; she has her hair the same, the sunglasses, the shoes. And that has been very powerful for her. Absolutely. It’s made her an icon.
Steve Jobs did that with his signature black turtleneck. And Obama too. He said he has a navy suit and gray suit, and he just alternated. It’s a uniform, and it also takes some decision-making out of the day.
The other thing that struck me about Anna was how she used silence as a kind of power? Anna never wastes a single breath or sentence on anything that doesn’t deserve her time. I have a scene in the book with Phillip Picardi, editor at Teen Vogue, pitching Anna and other executives at Conde Nast for some finances. Anna doesn't say anything during the whole meeting. The CEO is grilling Phillip on cost and budget and stuff. Finally, Anna just stands up and says how much money do you need? And he gives her a number. She turns to Phillip, shakes his hand, says congratulations, and walks out of the room. Just like cutting out all the bullshit, all the debate. You need $3 million. I'm going to get your $3 million.
Now it’s one thing to rise to success, but what is striking about Anna has been her ability to maintain her position for decades—and expand her power. From the book, it seems much of that comes from the smart alliances she’s fostered over the years. There are so many examples of this, many of them through philanthropy. In the early 1990’s she launched a fundraiser for AIDS. Nowadays that sounds great and normal, but at the time it was very controversial. It was significant getting Vogue involved and having Si Newhouse write a big check.
Then there’s the Costume Institute fundraising through the Metropolitan Gala. Over the years, Anna has grown the gala into the Super Bowl of red carpets. Everybody wants to go, and that gives her a lot of power. People see it as a platform, and they want to be involved in that.
Would you characterize her involvement in these charities as Machiavellian? No, not actually. But Anna always has a reason for what she’s doing.
Exclusivity is its own kind of power….curating it? Anna’s always been interested in that. If you just look at her growing up in London and going to the most exclusive nightclubs. In her magazine, she’s very specific about what she wants and doesn't want. Look at her having Madonna on the Vogue cover in 1989. At the time, only models were getting covers, and Madonna was controversial. It was a big deal, and we see her in a white swimsuit in the pool with simple styling. The issue sold really well.
That’s her secret sauce. She pushes things just far enough so that people stay interested, but not turned off.
Often Anna is characterized as cold and ruthless. For instance, she came into several magazines she ran and fired a lot of the staff straightaway? She doesn’t seem to get emotional about such things, but does this make her cold? I’m sure Elon Musk or Steve Jobs or Jeff Bezos—name any big businessman—probably makes these decisions all day, every day, to be successful. And if you get emotional about it, you can’t do it, and it’s harder to get ahead. There’s some truth to the argument that if Anna were a man, nobody would think twice about it.
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Also, I recently did a Q&A with Kate McKean about writing non-fiction for her newsletter Agents & Books. She offers a PhD in publishing with her posts—and hopefully I added a sliver of wisdom for her community. Here it is for those interested, and I’ll be interviewing Kate on her workcraft as a literary agent soon.
And finally, a little #CreativeCraft on Picasso. No doubt Anna Wintour would have flipped to work with this iconic painter, and I loved this video of him at work.
“Painting is a blind man's profession. He paints not what he sees, but what he feels, what he tells himself about what he has seen.” —Pablo Picasso
Have a nice weekend,