How'd Anna Wintour Do It? The Unauthorised Biography With An Answer

By Lisa Armstrong
Anna Wintour. Photo / Getty Images

It's not hard to imagine who the readers will be of Amy Odell's new book Anna: thousands of would-be Wintours, of course, parsing the pages to find out how she did it. "It" being the longest-ever continuing reign at the very top of the fashion tree.

There are almost 350 pages here, but the reader is left wondering whether the answer is a simple one. Perhaps Wintour, now 72, just recognised early on that power is often most effective when it is a caricature of itself, and that cultivating a Cruella de Vil persona would do her no harm at all.

Having the parents she did helped. Her American mother, "Nonie", from an affluent, East Coast Quaker family, gave Anna her social connections and a small family legacy that meant she could afford to take a break from jobs when pickings were thin. Handy. Her British father, Charles Wintour, was a successful editor of the London Evening Standard.

Chilly Charlie, as he was known his daughter would later be branded Nuclear Wintour instilled in her a ferocious work ethic, a fondness for Svengali-type older men (many of her boyfriends, including the gossip columnist Nigel Dempster, and her first husband, child psychiatrist David Shaffer, were significantly older than her) and an air of superhuman impassivity.

When Anna was 2, her big brother Gerald died in a hit-and-run. Charles, informed of the accident, returned to his meeting without saying a word to his editors.

Wintour later said she chose fashion because it was somewhere she could shine as much as her intellectual family had in their fields. As well as raising four children, Nonie was a literary critic; Patrick, another of her brothers, would become political editor of The Guardian. Naturally, Charles encouraged her to aim high, and set her sights on Vogue.

Yet despite his contacts, things were slow to ignite. As a teenager, she worked at that shoplifters’ paradise Biba, although the manager there remembers her as “very plain and very ordinary ... not the typical girl we would have hired”.

Eventually, she got her break at British Harpers & Queen. She decamped to New York aged 25 and there followed an unlikely stint at Viva, a sister magazine to Penthouse, which, despite Anna's labours, never quite managed to shake off its porno associations.

Everywhere she worked, she would, by her later admission, ignore her editor’s need for “credits” (where the clothes had been sourced) and disregard the readers’ needs for clothes they might actually like or wear. She was fired by three bosses in a row a trajectory that would have finished most people off.

But ... there’s something about Anna, and it’s not just the Stakhanovite work ethic. There’s her aura of Anna-ness, cultivated early on. A picture in this book of her aged 15 shows her with “The Bob”, ready formed.

The journalist Emma Soames, an old friend of Wintour’s, recalls that from the outset: “Anna’s power in those days, such as it was as a fashion assistant, lay in her silence.” The sunglasses and unfeasibly (for a lowly fashion editor) expensive clothes soon followed, as did the assistants who would move from job to job with her, paid by no one knows who.

Eventually, "Si" Newhouse, Condé Nast's owner-emperor, took notice and installed her at American Vogue. Just one problem. It already had a successful editor-in-chief in the form of Grace Mirabella. The two were left to slug it out before Anna was parachuted into British Vogue a magazine she considered a joke because the stylists there (guess what) ignored their editor's need for credits. Vogue House seemed like a dank backwater. "Oh my God, I'm back in England," she said.

Her British Vogue team were none too enamoured of her, either, particularly her 8am starts, abrupt manners and micromanagement. This is when she got the "Nuclear Wintour" nickname. On the other hand, most acknowledge that knowing what she wanted was a refreshing trait in a boss.

When designers failed to produce the micro-minis she had set her heart on for her magazine, she told her team to shear off the hems. She upped circulation albeit by a relatively modest 6,000 and increased ads.

Despite commuting weekly by Concorde to see her husband, who remained in New York, and somehow having two babies in that time, her 18-month tenure was a success. A year later, she would be given the top job at American Vogue; the outgoing Mirabella would learn of her dismissal via a gossip item on television, a similarly brutal send-off to the one suffered by her predecessor, Diana Vreeland, in 1971.

For all this book’s painstaking minutiae and journalist Odell has spoken to hundreds of sources we still don’t get a real sense of Wintour’s charisma, nor the glitz and grotesqueness of life lived at the highest, headiest levels. Instead, we get chapter and verse on rising and falling ad revenues or slightly turgid accounts about how “normal” Wintour is in her Long Island compound. What should scintillate reads like an end-of-year financial report.

Still, there are gems. Wintour is so wrinkle-averse that she once, Odell claims, had the fat under a baby’s chin airbrushed before it could be admitted on to the pages of her magazine. Standards are exacting. When a beauty editor suggested a feature on Gwyneth Paltrow’s Goop beauty line, Wintour’s response, claims Odell, was: “If you do it, just make sure we’re retouching her, because she’s looking quite rough these days.”

(Anecdotes such as this may owe more to folklore than fact; Wintour was not available for comment.)

If Wintour’s power was to mean anything to the outside world, she had to make fashion seem the most glamorous, glittering, exciting, moneyed place to be. Burn-out among her retinue of assistants was high, but higher up the food chain, key staff stayed in situ for years, cushioned by fabulous salaries and Anna-approved designer wardrobes, for which they were sometimes commanded to lose weight.

Through the Met Ball, through her notorious froideur (immortalised in The Devil Wears Prada, a badly written book no one thought would amount to anything before it became a blockbuster film), through her friendships with Puff Daddy, Kanye West, Serena Williams, Princess Diana, Hillary Clinton and the Obamas, Anna extended her power to the point where Hugh Jackman, Harvey Weinstein, Oprah (who lost 20lb in order to appear on a Vogue cover), Amal Clooney and Melania Trump (who sought her views on their wedding dresses) et al would court her advice.

“Anna has mercilessly made her best friends people who are the highest in their chosen fields,” wrote her friend the late André Leon Talley, in his 2020 memoir.

Yet it's not as though there haven't been missteps. During her very brief editorship of American House & Garden, a special hotline had to be installed to deal with irate readers wanting to cancel their subscriptions.

There was her oddly persistent support for fur, for John Galliano after his anti-Semitic rant, for the white, privileged socialites who comprised Vogue’s workforce for decades until Black Lives Matter. (“I want a princess,” she was once heard to say about her next assistant.)

There was the grimly hagiographic interview with Asma al-Assad that her staff begged her not to run. And there are the magazines she pushed for from Men's Vogue to Teen Vogue that have struggled or closed.

Anna is bigger than all of this. As the internet continues to diminish Condé Nast’s once impregnable glamour and potency, only Wintour remains undimmed, queen of well, no one quite knows what at this point. Only that she is one.


Anna by Amy Odell (Allen & Unwin, $40) goes on sale in NZ on May 30.

Share this article: