As US Vogue editor-in-chief, Dame Anna Wintour forever changed the fashion industry. But her enigmatic leadership saw her influence stretch beyond the magazine's pages.
For years, Dame Anna Wintour was an impenetrable force.
In the front row of any fashion show that mattered, Anna Wintour watched the runway, her eyes shielded from nervous designers whose livelihoods depended on what she printed.
She transcended the realm of fashion to become an icon in her own right – thanks in part to a helping hand from Hollywood.
"Across more than three decades' worth of issues of Vogue and its spinoffs, she has defined not only fashion but also beauty standards, telling millions of people what to buy, how to look, and who to care about," wrote fashion journalist Amy Odell in Anna: The Biography.
But even Odell, who interviewed hundreds of people about Anna Wintour, was taken aback at the complexity of her subject.
"People couldn't agree on many things about her, including whether she's an introvert or an extrovert, ruthless or just very demanding," Odell said on reflection.
"I couldn't get a consensus."
Now, as she steps down as editor of US Vogue after almost 40 years in the role, one thing seems clear: her legacy is as astonishing as her rise.
Like father, like daughter
Journalism was omnipresent in Anna Wintour's upbringing.
Her father, Charles Wintour, was the editor of the British newspaper The Evening Standard.
Anna Wintour's mother, Eleanor "Nonie" Baker, was also a reporter for a brief period.
Two of their five children would go on to work in media – Anna Wimtour at Vogue, with Patrick Wintour becoming The Guardian's diplomatic editor.
Even her step-mother, Audrey Slaughter, was a pioneering magazine editor.
As as respected newspaper editor, Charles Wintour's leadership style earned him the nickname "Chilly Charlie".
"He came from quite a Victorian upbringing, I'm not sure his mother ever spoke to him," Anna Wintour recalled in the landmark documentary The September Issue.
"He was also very private and very, in some ways, inscrutable."
It was Charles Wintour who decided his daughter should work in fashion.
"I can't remember what form it was I had to fill out. Maybe it was an admissions thing. At the bottom it said 'career objectives' and I said 'What shall I do? How shall I fill this out?'
"And he said, 'Well, you write that you want to be the editor of Vogue, of course.'"
Anna Wintour came of age in the 60s amid miniskirts, the pill and Beatle-mania.
"Growing up in London in the 60s, you'd have to be walking around with Irving Penn's sack over your head not to know something extraordinary was happening in fashion," she once said.
Predictably, she worked in a clothing boutique and enrolled in fashion classes.
Unpredictably, she quickly dropped out.
Jerry Oppenheimer, who authored the unauthorised biography Front Row, wrote that Anna Wintour's attitude at the time was: "You either know fashion or you don't."
It was in the 70s when she would get her foot in the door, becoming one of the first editorial assistants of Harper's & Queen.
But London was never the end goal.
After moving to New York City, she became a junior fashion editor at Harper's Bazaar in 1975 – but was fired nine months later.
She scored a job at Viva before the publication went bust only years later, then became the fashion editor for a new magazine called Savvy.
By the early 80s, she became the fashion editor at New York magazine.
But Condé Nast came calling, and two years later she joined the media giant as Vogue's first creative director.
'Nuclear Wintour'
When Anna Wintour joined Vogue, Grace Mirabella had been editor-in-chief for 12 years.
She loved the colour beige, and incorporated it in both her wardrobe and office decor.
But Anna Wintour's arrival wasn't the first time these two titans had met.
Back when Anna Wintour was making her mark at New York magazine, one of Mirabella's fashion editors, Polly Mellen, organised a meeting between the pair.
Vogue was doing the numbers, but could Anna Wintour give it some extra spice?
The meeting came to an abrupt end when Mirabella asked her what job she would like at Vogue, to which Anna Wintour replied: "Yours."
The newly established role of creative director came with a layer of vagueness, which Anna Wintour used to her advantage.
She was second in command, tasked with "enriching the looks of the pages".
In her memoir, Mirabella wrote that Anna Wintour would "go behind my back and redo layouts, bringing new art, circumvent me and my fashion editors".
She described Anna Wintour's tenure under her as "a very bizarre three years during which Anna created a kind of office within the office, working with Alex Liberman, with fashion editor Polly Mellen, with Jade Hobson, and against me".
Two years after joining Conde Nast, Anna Wintour took over British Vogue when Beatrix Miller retired in 1985.
As editor she replaced multiple staff members and exerted more control than any of her predecessors.
Like her father, she earned a frosty nickname – "Nuclear Wintour".
Years later, she would address the label in a rare interview with 60 Minutes.
"If I'm such a bitch then they must really be a glutton for punishment, because they're still here," she said.
"If one comes across as sometimes being cold or brusque, it's simply because I'm striving for the best."
In 1987, Anna Wintour returned to New York City with the task of revitalising Home & Garden in a bid to compete with rival publication Architectural Digest.
She reportedly cancelled $2 million worth of shoots in her first week, and made the publication nearly unrecognisable to readers after shortening the title to HG.
Subscriptions declined. Advertisers pulled out.
While some would be shown the door, gossip columnists proclaimed Anna Wintour had "failed upwards".
Because try as she might to ignore the constant swirl of rumours, Mirabella's own demise was hurtling towards her.
By the late 80s, Mirabella was perceived as "out of step with the times" as the younger, fresher Elle magazine gained ground.
In 1988, Conde Nast owner Si Newhouse sensationally ousted Mirabella.
Instantly, Anna Wintour was the editor of Vogue.
The winds of change
Anna Wintour's first Vogue cover made history for one clear reason – the model was wearing jeans.
Her debut featured model Michaela Bercu walking in the New York City sunlight, her eyes nearly closed as the wind fanned her blonde hair around her smiling face.
"It was so unlike the studied and elegant close-ups that were typical of Vogue's covers back then, with tons of makeup and major jewelry. This one broke all the rules," she reflected in Vogue in 2012.
The cover was so different from previous issues that the magazine's printers called asking if there had been a mistake.
"I had just looked at that picture and sensed the winds of change. And you can't ask for more from a cover image than that," she wrote.
While supermodels such as Cindy Crawford, Linda Evangelista and Christy Turlington regularly graced the cover of Vogue, Anna Wintour ushered in an era of celebrity worship.
"Anna saw the celebrity thing coming way before everybody else jumped on that bandwagon," Vogue's then creative director Grace Coddington said in The September Issue.
"And, you know, whilst I hated it, I'm afraid I have to admit she was right."
As Vogue editor, Anna Wintour earned a reputation for being as inscrutable as her father – or perhaps more.
"I think she enjoys not being completely approachable," Coddington said.
"Just her office is very intimidating. You have to walk about a mile into the office before you get to her desk. And I'm sure it's intentional."
Like Coddington, André Leon Talley worked alongside Anna Wintour for decades as the magazine's editor-at-large.
"She is not a person who is going to show you her emotions – ever," he said in The September Issue.
"She's like a doctor, she's looking at your work. It's like a medical analysis. Some of us can't cope with that. We need to be loved."
Anna Wintour has previously admitted she was not academically successful, revealing perhaps she spent "a lot of my career trying to make up for that".
But she is certain about one piece of advice she learnt from her father.
"People respond well to someone who is sure of what they want."
'Sheer brute force'
At Vogue, Coddington and Talley each had complicated relationships with Anna Wintour.
"I know when to stop pushing her. She doesn't know when to stop pushing me," Coddington said.
In his memoir, published two years before his death, Talley detailed the breakdown of their relationship after Amma Wintour retired him as the Met Gala's live stream correspondent and instead bestowed the role to a YouTuber.
"I have huge psychological scars from my relationship with this towering woman who can sit by the queen of England, on the front row of a fashion show, in her dark glasses and perfect Louise Brooks clipped coiffure, framing her Mona Lisa mystery face. Who is she?" he wrote.
"What drives Anna is a sense of her own ability to survive as a powerbroker, with sheer brute force, and to sustain an extraordinary level of success."
Praise from Anna Wintour wasn't entirely unattainable – but it was concise.
Her seal of approval on the final copy of Vogue articles was a Post-It stuck to the bottom of a printout simply reading "AWOK" – Anna Wintour OK.
"Whisper the phrase, 'You've been Awok'd' into the ear of an unsuspecting Vogue staffer, and he or she is likely to breathe a heavy sigh of relief, or maybe even bust out a happy dance, with hands raised in the air," Vogue writer Chioma Nnadi revealed in 2017.
AWOK or not, one of Anna Wintour's former assistants turned her experience into a novel, with Laura Weisberger writing The Devil Wears Prada in 2003.
The novel, which follows a young woman hired as the assistant to a demeaning and demanding fashion editor – became a best seller and inspired the film of the same name.
When the elevator doors slid open to reveal Meryl Streep as the frosty editor, complete with dark sunglasses and pursed lips, it solidified Anna Wintour's icon status in the pantheon of pop culture.
The first Monday in May
The Met Gala as we know it today wasn't always the biggest night on the fashion calendar, nor did it garner more attention and cultural significance than the Academy Awards.
In its first incarnation, the Met Gala was a simple midnight supper for New York's elite held in a bid to raise money for the Metropolitan Museum of Art's struggling Costume Institute.
The event started in the 40s with socialite Eleanor Lambert as its driving force.
But it was brought to life in spectacular fashion in the 70s by then-Vogue editor Diana Vreeland.
The Met Gala gauntlet was then passed to Anna Wintour in 1995, seven years into her tenure.
US media have reported she will remain as editorial director at Vogue and global chief content officer at Conde Nast.
It's unknown yet how this could her legacy at the Met Gala.
Under Anna Wintour, the Met Gala embraced celebrity culture more than ever before.
Andre Leon Talley described the event as "the Super Bowl of social fashion events" through the way it brings together the biggest names from sport, politics, business and social media.
While tickets once cost $50, brands now fork out hundreds of thousands of dollars to book a single table.
Undoubtedly, Anna Wintour transformed the Met Gala as a money-making machine for the Costume Institute, Vogue and the industries it feeds.
In her role at the helm of the Met Gala, Anna Wintour has raised over $US250 million for the Costume Institute.
"It just grew over the years. I can't pretend there was a grand plan or a grand strategy," she once said.
Over the course of her record tenure, Anna Wintour came under fire for what featured in the pages of Vogue and what didn't.
"Nobody was wearing fur until she put it on the cover in the early 1990s", Vogue's Tom Florio once said.
"She ignited the entire industry."
Anna Wintour was frequently targeted by animal rights groups for making fur fashionable and said she had "lost count" of the amount of times she had been physically attacked by activists.
After a tofu pie was lobbed her way outside a Chanel show in Paris in 2005, she was asked what she would do following the incident and reportedly replied: "Wear more fur."
Anna Wintour's remarks around weight also caused controversy on more than one occasion.
Andre Leon Talley revealed on the Oprah Winfrey Show that Anna Wintour had demanded he lose weight.
"Most of the Vogue girls are so thin, tremendously thin, because Miss Anna don't like fat people," he said.
In The September Issue, after Coddington asks the documentary's camera operator to be involved in one of the glossy spreads, Anna Wintour told him he they would need to photoshop his stomach.
But it was in the summer of 2020 when Conde Nast faced a reckoning.
After George Floyd's death at the hands of police sparked nation-wide unrest and protests, she apologised to staff for "publishing images or stories that have been hurtful or intolerant".
In the company wide memo, Anna Wintour admitted there were too few employees of colour and took full responsibility for mistakes made.
"I want to say plainly that I know Vogue has not found enough ways to elevate and give space to black editors, writers, photographers, designers and other creators."
When her father, Charles, retired from newspaper publishing, she asked why he was leaving.
"He was obviously so passionate about what he was doing, and he said 'Well, I get too angry,'" she said.
"So I think when I find myself getting really, really angry that it might be time to stop."
Anna Wintour's replacement is yet to be announced.
Yet she is likely the last of her kind.
While issues will still be printed and newsstands will still be stocked, digital content has disrupted traditional media.
And it is unlikely we will ever see another singular gatekeeper of fashion with as much global influence as Anna Wintour.
