‘Anna’ reveals an unseen side of fashion’s most influential figure

Marianna Cerini

“The amazing thing about Anna is the average person knows who she is,” designer Tom Ford tells fashion journalist Amy Odell in the first pages of “Anna,” a new biography of American Vogue editor-in-chief Anna Wintour out this week. “You show them a picture and they say, ‘That’s Anna Wintour from Vogue.'”

Wintour, who has been at the helm of fashion’s most influential magazine since 1988, is a household name not just in the industry, but across culture at large.

She’s been the subject of documentaries and the inspiration for movies, as talked about as the celebrities she’s put on her covers (rumors she was about to leave Vogue back in 2018 fueled a flurry of wild speculation online) and as immediately recognizable, thanks to her power bob and ever-present sunglasses.

“Anna,” which Odell began writing in 2018, charts Wintour’s rise, tracing her formidable career from 1960s London to one of the most powerful positions in media today. To try to paint a full picture, Odell interviewed over 250 sources — some of whom requested anonymity — and browsed through archival records and past coverage of the undisputed queen of fashion.

The final product is a sprawling, comprehensively reported piece of nonfiction (there are some 80 pages of footnotes) that mixes insiders’ anecdotes — Andy Warhol considered her a “terrible dresser”; Bradley Cooper sought her advice on whom to cast in the lead role of “A Star Is Born” — with a highly detailed and revelatory portrait of a very private figure.

“The goal was to draw a picture of Anna’s legacy, her triumphs and troubles, and explain the ingredients to her clout and success,” Odell said in a video interview. “Getting to the top is one thing, but staying there is quite another. Anna has been at Vogue for 34 years. In a business like hers, that’s extraordinary. I wanted to explore how she has managed to have this incredible longevity.”

Two sides of Anna

Including accounts from close friends, designers and collaborators; letters written by her father, the Fleet Street editor Charles Wintour; and insightful descriptions of just about every professional and personal decision Wintour ever made, “Anna” shows different sides of the influential editor-in-chief.

Odell starts from the very beginning, introducing Wintour’s privileged upbringing — her family was well-connected in the UK’s literary world, and Wintour had access to a generous trust fund — and recounting how she drifted into journalism, first in London and then in New York, where she eventually landed the top role at Vogue.

As she climbed further into the world of publishing, Wintour appeared at times quietly driven, at times ferocious in her ambition to turn Vogue and herself into an iconic brand (one of her most defining traits is her discipline: her day starts at 5.30 a.m.; her weight doesn’t seem to have changed since she was 18. After she’d had a facelift at the end of 2000, Odell writes, she went back to the office with yellow bruises still visible instead of resting at home, because she never misses work.)

She is “brutal” in her approach to editing, staying in the office until midnight to review layouts and make edits; “unsparing” in her commentary on the photos in “The Book,” the mock-up version of the magazine she has final say on; “militant” in her planning of the Met Gala, for which she oversees every detail, including the guest list (“you just can’t buy your way into it,” Odell said) and the menu (she’s banned chives, garlic, onion and parsley).

“Her directives were often so absurd the Met team just laughed them off,” Odell writes about Wintour’s approach to the fashion event. “Once, when walking through the Egyptian galleries, where the display cases were empty because they were being replaced, she turned to the Met team and said, ‘Where is she? Yes, you — can you go into the basement and just bring up a bunch of art and put it in these cases?'” (Wintour has a habit of not learning the names of the people who work under her, including her assistants and some of the museum staff.)

But she’s also a dog person, a doting grandmother who changes diapers and loves to entertain, and a committed philanthropist (“there is a person there,” Wintour’s longtime Met Gala planner Stephanie Winston Wolkoff tells Odell in the book).

For Odell, this dichotomy was one of the most fascinating aspects of writing about her subject. “What struck me during the course of my research was how complicated Anna is as a person,” she said. “People couldn’t agree on many things about her, including whether she’s an introvert or an extrovert, ruthless or just very demanding. I couldn’t get a consensus.”

The last editor of her kind

Wintour herself didn’t shed any light on which “Anna” she most identifies with. Despite multiple interview requests, the fashion figure declined to speak to Odell for the book.

Still, Odell noted, she didn’t shut it down.

“When I started working on ‘Anna,’ people told me it could go two ways: She would try to stop me, maybe warning sources not to talk to me, as she had done with a previous unauthorized biography; or she would help. The latter group turned out to be correct,” she said.

A year and a half into the project, with some 100 interviews under her belt — mostly from Wintour’s early life and career, as those sources “seemed to be less skittish about talking to me,” Odell said — she received a call from the Condé Nast public relations team.

“Anna had heard about the book, and she wanted to have more details about it,” Odell said. “I explained that I wanted to write about a woman in a unique position of power. After that conversation, her office sent over a list of names of her closest friends and colleagues I could reach out to — Tom Ford, Hamish Bowles, Serena Williams. I took it as a kind of endorsement.”

Access became easier after this, Odell said, although not everyone wanted to talk on the record.

While Wintour’s been the subject of much gossip throughout her career, Odell noted that she hasn’t done a whole lot to correct the narrative around her. “I think in her mind, she has a job that she loves and she’s going to run hard at it every single day,” Odell said. “That’s really what drives her.”

That, and the fact she’s probably the last magazine editor of her kind. As the media and publishing industry continue to be disrupted by the rise of digital content, influencers and social media, it’s unlikely there will ever be another singular fashion gatekeeper as globally relevant as Wintour. She’s aware of it too: Over the past decade, despite coming under fire for failing to foster diversity and inclusivity at Condé Nast on behalf of its progressive workforce, she has in fact expanded her role, becoming artistic director of Condé Nast in 2013, the company’s global content adviser in 2019, and worldwide chief content officer and global editorial director of Vogue in 2020.

“Anna has always been a step ahead of everybody else in the business,” Odell said. “She’s at the top of the pyramid. It’ll be interesting to see what happens when she does leave her job — though I am sure she already has her exit planned to perfection.”

Add to Queue: Five stylish memoirs and biographies

READ: “Alexander McQueen: The Life and the Legacy” (2012)

Judith Watt’s critically acclaimed biography takes readers from the designer’s early East London life and student days at Central Saint Martins to his ascent as one of fashion’s most iconic names and his untimely death at age 40. Delving into McQueen’s inspirations, passions and struggles, it’s a compelling read that offers an honest, multifaceted portrait.

READ: “Grace. A Memoir” (2012)

Anna Wintour’s second-in-command for over two decades, Grace Coddington, charted her life and career in this intimate memoir, recounting her rise from fashion model in the 1960s and ’70s to creative director and chief stylist of American Vogue.

READ: The Vanity Fair Diaries (2018)

Former Vanity Fair editor-in-chief Tina Brown spilled all in this in this brilliant memoir about her tenure at the storied magazine. Infused with stories of glamor and gossip, office dynamics, and the personal challenges that come with being a working mother, it’s a fascinating chronicle of the publishing world’s glittering past.

READ: Champagne Supernovas: Kate Moss, Marc Jacobs, Alexander McQueen, and the ’90s Renegades Who Remade Fashion (2015)

Veteran pop culture journalist Maureen Callahan explored the pivotal history of fashion in the 1990s, told through the lives of icons like Kate Moss, Marc Jacobs, Alexander McQueen, and other tastemakers who defined the decade in terms of style, culture and artistic output.

READ: The Chiffon Trenches: A Memoir (2020)

The late André Leon Talley’s memoir is more than a candid look at the who’s who of the past 50 years of fashion; it’s a narrative that weaves the struggle of being a person of color in America’s publishing industry with anecdotes about his upbringing in the South and reflections on the importance of his faith.

Top image: Anna in Jamaica working for Harper’s Bazaar in 1976.

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