— The Biography
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Introduction
With so few women having attained Anna’s level, there’s no model for how that should look, just the feeling that such power should be exercised with a warmer touch than she naturally possesses. (Though if a man did her job as well and with similar affectations, his discipline and commitment would likely be celebrated.)
As her longtime Met Gala planner Stephanie Winston Wolkoff put it, “There is a person there.”
Some who have worked closely with her think her strengths are actually twofold: first, managing creative people and the creative process, and second, forming politically savvy alliances to grow her power.
Chapter 1: Origins
A successful editor, he thought, must “accept more invitations than he wants and know more people than he likes.”
her cynical nature as a form of “self-protection, because I think she was extremely vulnerable.”
Chapter 4: Anna Wintour, Fashion Assistant
“Anna’s power in those days, such as it was as a fashion assistant, lay in her silence,”
it wasn’t Anna’s style to have an outright disagreement with somebody—she hasn’t ever been confrontational and would continue to avoid direct confrontation throughout her career.
Chapter 5: A New Start In New York City
“I felt quite isolated growing up in England, not because of family but with it being such a class-driven culture, and one of the things I like here is that it is not all about class and where you went to school and what your parents do, and everyone in New York is from somewhere else, and that creates a very positive force,” she said. Yet Anna would, many years later, seem to place outsize weight on family and educational background when hiring at Vogue.
Hiro, the legendary surrealist fashion photographer
Chapter 7: A Savvy Move
Ambition aside, Anna couldn’t relate to them. Unlike the target Savvy reader, she had entered an industry where her femininity was an asset rather than a handicap.
Chapter 8: In Vogue
Mirabella asked Anna what job she would like at Vogue, and Anna replied, in what she later described as “a sudden fit of candor” that was unlike her, “Yours.” That ended the meeting.
Chapter 9: Second Best
All of this was in line with Anna’s determination to place fashion within the context of culture, in order to push fashion onto a higher plane of significance, the same way she sought to elevate herself.
Despite living her life in the spotlight, Anna has never cared to be the center of attention.
Chapter 10: A Tale Of Two ‘Vogue’S
dismissing goings-on at the magazine as silly ladies’ stuff and casting Anna as “Nuclear Wintour” and her tenure as “Wintour of Our Discontent” was largely sexist, and the scrutiny of her merciless methods far outstripped that bestowed on male executives.
“People misinterpret her focus for coldness. But she’s not cold, she’s generous to a fault,”
Chapter 13: Calculated Risk
But that morning, when she got to work, she assembled her staff and told them that anyone who believed she had gotten to where she was by sleeping with her boss “is still living in the era when a woman could only make it to the top by pleasing a man. This is the 1980s. You don’t have to do that anymore.”
The infamous hours-long run-throughs were now over in minutes. Seymour said, “Anna would just go, ‘Yes, no, yes, no, yes, no. Good-bye.’
“She loved humor in writing. Some people say she has no sense of humor. I know that is not true.
“The fact that that very nice man that I sat next to on the plane thought that it would be completely wrong to put Madonna on the cover and completely out of keeping with the tradition of Vogue being this very classically correct publication pushed me to break the rules and had people talking about us in a way that was culturally relevant, important, and controversial, all of which you need to do from time to time,” Anna said. Her instinct paid off. When the Madonna issue came out, it sold 200,000 more copies than the previous May issue edited by Mirabella. It foreshadowed a sea change in fashion, which soon would replace models with celebrities as the faces of the industry.
Chapter 14: “In” Versus “Out”
Seventh on Sale ended up raising more than $ 4.7 million, all of which went to the New York City AIDS Fund. There was no ostensible business purpose to Seventh on Sale. No sponsorships were sold, no magazine coverage was sold to an advertiser. Anna’s staff thought that she viewed giving back as part of what she and Vogue should do. But in an article about magazines raising money for charity, the Wall Street Journal suggested otherwise: “On the charity ball circuit, there’s a new catchword: ‘cause marketing.’ In a difficult advertising environment, with many traditional forms of promotion exhausted, publishers are adopting causes ranging from AIDS to homelessness and breast cancer as their favorite charities.”
The final mark of approval on stories, her initials plus OK—“ AWOK”—became a verb in the office. “Is it AWOK’d? Is it AWOK’d yet?” editors would parrot in frustration.
Chapter 15: First Assistant, Second Assistant
New Yorkers love all-black, fashion people love all-black, fashion designers love all-black.
When second assistants started, they received a twenty-one-page manual reviewing everything from how to handle expenses to maintenance of Anna’s home.
Chapter 17: Follow The Money
“Perhaps this is the moment for me to confess that, yes, I wear fur. I also eat juicy steaks. If you are appalled at my political incorrectness, you should know that I, for one, don’t see any difference between raising animals for hamburgers and farming mink for coats.”
there was the instance when Brooks was designing the circle garden, so named for its shape, and said, “You could lie on the grass and look at the moon here.” Anna replied, “I am never going to lie on the grass and look at a full moon.”
“I just felt like there’s such an epidemic of obesity in the United States. And for some reason everyone focuses on anorexia.… We need to spend money, time, and education on teaching people to eat, exercise, and take care of themselves in a healthier way.”
her decisions about casting models and cover subjects for Vogue stemmed mostly from instinct about what would resonate with her audience, rather than feeling she should make special effort to spotlight people from underrepresented groups. Many years later, Anna would—as she did when switching from model to celebrity covers—take a completely different approach to diversity in Vogue.
“She deserves a lot of credit, which I don’t believe she gets, for taking a wild risk to use her name and reputation to push a very unwilling fashion industry into the digital age,”
Chapter 18: The Divorce
looks didn’t seem to be what Anna primarily admired in men; after a lunch with Bill Gates, when Microsoft was on the rise, she came back to the office and told Laurie Jones how attractive she thought he was. Jones just thought, God, she’s attracted to people who are powerful.
It might have been true that Bryan made her more interested in politics and political fund-raising, but it was routine sexism to pin the desires of a remarkably powerful woman on the accomplishments of her new boyfriend. “She had strong political opinions already,” Bryan said. “I didn’t have to do anything.”
Chapter 20: A New Alliance
What if that was just our approach? You would sit with people and tell them if you like something or didn’t like something and why, but you did it like you were talking to your daughter. We don’t do it in a dismissive way.” “Why would we do that?” she wanted to know. “Because if you do that, then you’ll be like the McKinsey of fashion,” Florio said. “We’ll have a value proposition that’s so much bigger than losing business because of us not writing people up.”
Chapter 21: Mutual Benefit
“Resist any cheapening of the brand, however popular and lucrative it might be in the short term”—referring to Vogue passing on the show. “Vogue is not in the business of making entertainment out of the struggles of new designers. We’re in the business of nurturing the next generation of American talent.”
“Where a lot of her power stems from is that she’s so generous to so many people,” Hernandez said. “She does so much for so many people that when she asks something of you, you do it.
Chapter 24: Politics And Pain
“Imagine my amazement,” she wrote in her editor’s letter, “when I learned that Hillary Clinton, our only female presidential hopeful, had decided to steer clear of our pages at this point in her campaign for fear of looking too feminine. The notion that a contemporary woman must look mannish in order to be taken seriously as a seeker of power is frankly dismaying.
Chapter 25: Anna Wintour, Artistic Director
This sort of recognition for her philanthropy was what Anna had told friends she really wanted as her legacy—more than fame in publishing or additional magazines to run back at the office.
“What do you think of Throwback Thursday?” Blanks asked. Style.com had been running a video series with footage it had licensed from Fashion File, his old TV show, of old runway shows by designers like Helmut Lang and Claude Montana. “Irrelevant,” Anna said. “Why? It’s the most popular thing we have on the platform,” Blanks said. “Nobody wants to go back into the past. You have to go into the future,”
Chapter 26: Changes
Most advertisers didn’t want to market to teens, who were viewed as not having significant disposable income. And besides, teens don’t even want to identify as teens. This was why Teen Vogue’s audience was always pitched as 16-to 24-year-old women who were in college or getting their first job.
James added nuance and perspective to elements of the business that had been ignored or taken for granted by the majority of those running labels, stores, and magazines, such as “using fur, which is a controversial thing amongst white people who don’t understand Black African culture and farming. So that’s about people wanting to put their own moral compasses onto other cultures, which is a type of colonialization being disguised as being progressive.”
Welteroth wrote in her memoir More Than Enough about the day she became editor of Teen Vogue: “I have thought back to that moment many times and grappled with a sense of shame and even blame over how powerless I felt in what from the outside looked like the most empowered moment in my career. Even years later, it’s hard to untangle one feeling from the other.”
Epilogue: The Pandemic
what seemed to be missing from this conversation was acknowledgment that while Anna had made mistakes and operated in a largely exclusive way over the course of decades while she was in power, she was also a product of the company. She worked for men like Alexander Liberman who expected staff to be attractive. She worked under the auspices of research that purported to tell editors exactly which magazine covers would sell, which historically didn’t include people of color. For Anna, having been so rewarded for aligning with these values, any incentive to question them probably only would have come from within.
“If you’re trying to climb a social ladder in New York and you’re trying to get invited to the Met Gala, that’s something different. You’re never going to be able to feel success. You’re always going to feel unsuccessful. If you’re just looking for powerful people’s validation, then that’s a whole different ball game that you’re playing. But if you’re talking about a love of clothing, a love of expression, a love of color, a love of culture, a love of how putting things on can make women feel about themselves and their place in the world, those are measures of success that no one woman is ever going to be able to stop someone from feeling.”
She is, in a capitalist society, exactly the kind of person a company like Condé Nast wants to keep at all costs, no matter how many lower-level workers think she should resign, and no matter how exclusionary her management style has been.