Is Anna Wintour Really a Tyrant—or Something Else Entirely?

From a New York Times review by Willy Staley of the book by Amy Odell titled “ANNA: The Biography”:

In the very first pages of “Anna,” a semi-authorized biography of the Vogue editor Anna Wintour, the protagonist cries. It is Nov. 9, 2016, the morning after her erstwhile pal Donald J. Trump was elected to the presidency, and Wintour is speaking at a hastily arranged all-staff meeting. In the course of inveighing against a Women’s Wear Daily article that accused her of going too far in her support for Hillary Clinton, she cracks. This sort of peek into the soul that inhabits the iconic bob and sunglasses is what the book promises. On the cover, Wintour smirks from behind her armor, her arms crossed defiantly, as if challenging the reader to pierce the veil. The author, Amy Odell, tries valiantly.Is Anna Wintour

The book is the product of over 250 interviews and exhaustive archival research: into the letters of Wintour’s father, the Fleet Street editor Charles Wintour; into just about every fashion spread Anna put together over the course of her lengthy career, including those at the obscure Viva, a Penthouse-owned skin mag for ladies that Wintour attempted to clean up in the late ’70s. Odell even turns up a spread from a 1969 issue of a fashion magazine published by a young Richard Branson, in which Wintour, misidentified as “Anna Winter,” models the “Swinging London” styles of the day: a minidress, a trouser suit and a midriff-exposing triangle top. There are about 80 pages of footnotes, bringing the biography to a page count of nearly 450 — long, in one sense, but also about half the size of Vogue’s biggest-ever September issue.

Odell’s extensive reporting dredges up a wealth of delightful details: the time Wintour scandalized her boss by featuring a $9,000 goatskin trunk in New York magazine, where she also became known for throwing her pennies in the garbage; that Andy Warhol considered her a “terrible dresser”; that she would often bump into people while rounding corners at the Vogue offices because, “being a Brit, she used the other lane”; that after she went on a lunch date with Bill Gates, she told a colleague “how attractive she thought he was”; that “she once asked her photo department to retouch the fat around a baby’s neck.”

“Anna” is a biography with naturally completist goals, so these details are scattered across a sprawling work that sometimes, well, sprawls. And because fashion prefers the high-bred and European, names spill forth as if from a Pynchon novel: Francine du Plessix Gray, Lisa Love, Rochelle Udell, Min Hogg, Carlyne Cerf de Dudzeele, Peggy Northrop and Elisabeth von Thurn und Taxis, who descends from people who actually do feature prominently in “The Crying of Lot 49.”

But Odell rarely achieves sufficient altitude to situate Wintour in the flow of history — to fill in the background and the floor underneath her Manolo Blahnik shoes. Our subject does this, and our subject does that, but I wished at times that the focus on her would loosen just a bit, because Odell’s insights into how fashion magazines work (or worked) are fascinating when they arrive. (For example, sometimes editors will deliberately misattribute makeup that was used in a fashion spread to a dedicated advertiser, to keep them happy.) You’ll walk away knowing every step — and misstep — in Wintour’s famous ascent to the heights of magazinedom, but without a working theory of the case, no conceptual framework to pack it all into and remember it by.

One striking element of the reporting on the early stages of Wintour’s career — as a fashion editor at Harper’s Bazaar and a mostly forgotten magazine called Savvy — is how those who doubted or even fired her when she was younger later scrambled to deny it. And at times, the profound pull of her power seems to distort Odell’s efforts. I found myself underlining the insane qualifications that entered the record on Wintour’s behalf. Her former creative director Grace Coddington denies ever having quipped that André Leon Talley, the late Vogue editor at large who helped Wintour pick outfits, was “the only person who’s seen her in her underwear.” (Obviously a joke; Odell turns up a rather impressive dating history.) A former assistant says her job was so exhausting she would often lie prone on the floor when Wintour was at lunch, but adds, “It must have been a thousand times worse for Anna”; another admits that she “would also be annoyed if her coffee was late.” And yet another former colleague rebuts the claim Wintour has no sense of humor: “I know that is not true. She laughs and everything.” Wintour’s landscape architect says that a set of Times photos of the gardens at her compound on Long Island made it look too disheveled, when in fact that level of scruff actually requires constant maintenance. OK! Whatever! You almost want to splash cold water on these people’s faces.

Fashion people are different, of course; they all must know on some level that their power is both arbitrary and temporary — unless you’re Wintour — so both fealty and cruelty become necessary tools of the trade, to maintain order. They’re like knights or samurai in that way. But Odell doesn’t seem to have her mind made up about Wintour: Is she a cold apparatchik of this harsh industry, or an exacting, driven and visionary boss who is subject to sexist double standards? The text leans toward the latter interpretation, but includes anecdotes that provide grist for the former, and together these forces obscure as much as they reveal.

The resulting portrait is vexingly quantum: one moment packed with fantastic morsels of gossip, and at others strikingly obsequious. Whether Wintour really is a tyrant or something else entirely seems to depend on whom you ask — and Odell asked a lot of people. Well, you could probably say the same of a lot of editors. Even normal people, too.

Willy Staley is a story editor for The New York Times Magazine.

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