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What’s behind Anna Wintour’s Chanel sunglasses? We may never know

Anna Wintour arrives at the ‘America: An Anthology of Fashion’ themed Met Gala, at the Metropolitan Museum of Art in New York City, US, May 2, 2022. Picture: Andrew Kelly Reuters

Anna Wintour arrives at the ‘America: An Anthology of Fashion’ themed Met Gala, at the Metropolitan Museum of Art in New York City, US, May 2, 2022. Picture: Andrew Kelly Reuters

Published May 21, 2022

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Robin Givhan

Amy Odell’s biography of Anna Wintour, the renowned editor-in-chief of Vogue, approaches 500 pages, nearly 100 of them composed of endnotes.

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Odell reviewed the clips, searched the archives, interviewed former assistants, spoke to a fleet of Wintour’s friends, acquaintances and colleagues, as well as ex-boyfriends.

Yet the ultimate findings in “Anna: The Biography” feel rather slim and mundane, which may actually say more about the mythology surrounding the subject than the skill and tenacity of the author.

The version of Anna that lives in the popular imagination is far more intriguing than the flesh-and-blood reality — at least as Odell portrays her.

All who know her — and even those who don’t — are compelled to refer to her simply as Anna. She has risen to shorthand nomenclature by virtue of her longevity at the helm of Vogue, her impact on the fashion ecosystem and her expansive reach into the culture.

She is the empress of the Met Gala, the glittery political bundler, the publishing executive who refused to step down in the face of social justice protests levied against Condé Nast magazines and who, instead, declared her determination to right the corporate ship. She is Anna.

Odell documents her ambitious rise through the ranks of corporate fashion, from the British publishing world to New York magazine and HG, to American Vogue, where Odell worked for her briefly and, finally, to the top of the Condé Nast pyramid, as its chief content officer.

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As a junior editor and a stylish young woman, Anna had an obsession for telling details, a characteristic that has served her well in a highly visual and chaotic industry like fashion, but has also been a source of irritation and frustration for those with whom she worked — and later for those who were accountable to her.

As the inspiration for the unyielding editor in “The Devil Wears Prada,” Anna’s impatience for tardiness, meandering meetings and work that isn’t up to her standards or in line with her taste was made plain.

She doesn’t adhere to the management philosophy that advises bosses to sandwich criticism between two generous, self-esteem boosting compliments. From the earliest days of her professional life, Anna would get directly to the meat of the matter.

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But she also dislikes confrontation. These last two traits are forever in tension.

“Anna’s appointment to British Vogue was instantly controversial,” Odell writes. Her predecessor, Beatrix Miller, “was said to have run her magazine like the headmistress of a girls’ boarding school.”

Anna, on the other hand, ran it “with unprecedented, iron-fisted discipline. She wanted the staff to be on time, work hard, and run everything by her for approval, a stark departure from Miller, who allowed photographers to come into the office and select their photos, and approve their layouts.”

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Readers learn that Anna is a decisive and demanding boss — abrupt at times, yet often dryly witty. She’s a canny and perceptive business person, if not always as sensitive, sentimental or empathetic as society expects a woman to be.

She’s an attentive parent to her two children and a proud grandmother. She cried after Hillary Clinton lost the presidential election in 2016. She can be a loyal friend but she has also been known to let old friendships lapse.

Odell points to Wintour’s relationship with her childhood friend Vivienne Lasky as a prime example: “Anna invited her for tea, but Lasky didn’t get the impression Anna had any interest — despite her professed feeling of isolation — in reconnecting with an old friend.

The meeting was icy; Anna, who wore all-black, didn’t offer Lasky anything to eat or drink until her mom showed up later and told her to. That meeting marked the end of their friendship. Anna had moved on.”

Anna had other failed relationships, too.

Anna Wintour.

These things are mildly interesting, but not particularly unique. There are sad and unfortunate events in the great scheme of her life, but nothing cataclysmic.

If Anna has made some deal with the devil to achieve success, Odell did not produce the signed and smoking contract.

What we learn is that Anna is flawed, as well as hard-working and with a knack for reading the room, which makes her a complicated person but not the diabolical fashion tyrant of people’s imagination.

If she has an inherent gift that separates her from her rivals, it’s her ability to see herself as others do. She has used that invaluable knowledge in ways that are manipulative and beneficial.

If she terrorises assistants, designers or publicists, it may sometimes be because she can smell their fear or worshipfulness. Exploiting either — or both — helps her get what she wants faster and with less hassle.

The most satisfying biographies are those that help readers understand the motivations of its subject, that reveal the substructure of intriguing public personalities; and Anna is certainly intriguing. What lurks behind those Chanel sunglasses?

Odell, a former fashion magazine editor and author of the eye-opening “Tales From the Back Row,” begins at Anna’s beginning: her parents. Her mother Nonie Wintour (born Eleanor Baker) was American and part of a wealthy Quaker family.

The bullet points of Nonie Wintour’s lineage include a father who was a Harvard Law School professor, her own graduation from Radcliffe in 1938, and a family trust that helped to support her and her descendants.

Nonie met Charles Wintour, who was born in Dorset, England, when the two attended Cambridge. They were introduced by Arthur M Schlesinger Jr, the historian and presidential speechwriter. Eventually Nonie became known for her interest in public service, and Charles turned to journalism and built a reputation as “chilly Charlie” because he was such a tough and distant editor.

If there was a singular emotional gut punch during Anna’s childhood, it was the death of her older brother Gerald. On his way to school one morning, he was struck by a car when he was only 10. The crash fractured his skull and he died soon after he was rushed to a hospital.

Such a tragedy cracks the foundation of a family, and Odell reports that both parents were burdened by grief and guilt. It’s unclear how Gerald’s death affected Anna as she grew older.

While she may have been too young to fully grasp the tragedy at the time, she would have borne witness to the impact the loss had on her parents.

How did Anna come to understand heartbreak and responsibility? Only she can fully answer that question and there’s no indication that she sat for an on-the-record interview.

But the many people who speak for her and about her fail to provide much insight. Perhaps the lesson Anna learned was to be stoic and keep the full breadth of her emotions to herself.

Odell traces Anna’s interest in magazines to her father. There is an often repeated story that Charles Wintour essentially told Anna that her professional goal in life should be to run Vogue magazine.

But Odell offers anecdotes that underscore Anna’s early affection for fashion, from her time working retail at Biba in London to a brief whirl as a model. Odell attributes Anna’s focus on philanthropy to her mother.

But Odell never really gets behind those Chanel glasses to give the reader an understanding of what it means to walk in Anna’s shoes. There’s a coolness to the prose that matches the subject’s public persona.

That detached style doesn’t really help us gain much insight into Anna. We learn a lot about what she has done and what she has said, but very little about why. We’re never invited to warm up to the book’s subject, to either root for her or against her.

For all of the familiar fashion names that are quoted in the biography, one wishes there was someone who could look at Anna and put her into perspective. She’s a cultural figure, as much as a fashion one.

Would her personality be the stuff of tell-all memoirs and Hollywood films if she was in tech or politics? Or would she just be one more impressive ego in the sandbox? Is there something about fashion as an industry that fed the Anna mystique?

Is fashion, an industry anchored by women and gay men, such a victim of stubborn cultural stereotypes that the domineering, fearsome editor is just an eternal archetype? It may be that someone is always doomed to the part, or rewarded with it. Did Anna simply make peace with being the anointed one?

That’s the gnawing question. And it’s the one “Anna” never answers.

Robin Givhan is senior critic-at-large writing about politics, race and the arts. She is a 2006 Pulitzer Prize winner for criticism.

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