Sweeping through the doorway at Vogue’s sleek Manhattan offices, Anna Wintour surveys the room with a practised, critical eye.
There is a moment’s deliberate pause, a flash of obvious distaste. ‘Why,’ she snaps, ‘are there so many white people in the room?’
It could so easily be parody. After all, the legendary 71-year-old Vogue editor – with her signature sleek bob and sunglasses – has many times found herself the subject of ruthless satire, most notably in the film, The Devil Wears Prada.
Anna Wintour with Edward Enninful, the first black man to be British Vogue’s editor-in-chief and European editorial director of Condé Nast
But insiders at the world’s most glamorous magazine insist this ‘new Anna’ is all too real – the fashion queen once accused of promoting a ‘white-centric’ universe from a glass-fronted New York skyscraper, has turned woke.
As one former colleague told The Mail on Sunday: ‘Anna has gone from being the epitome of a white, privileged woman to the champion of diversity.
She’s the first to look at a magazine layout and ask whether there are enough black and minority models, stars and photographers.’
Another peeved insider adds: ‘She does it all the time, she’s known for it.
‘She walks in a room and says, ‘Why is this room so white?’ For someone who propagated white culture for decades, it’s a bit rich that that’s her new phrase.’
Wintour, who turns 72 this week, has spent five decades in fashion, dedicating her life to the whims and diktats of the catwalk and seems to have lived by the maxim ‘you can never be too rich or too thin’.
But this latest transformation is her most ambitious and fashion-forward yet. It is also perhaps her least likely.
The legendary 71-year-old Vogue editor – with her signature sleek bob and sunglasses – has many times found herself the subject of ruthless satire
Wintour at the opening night of ‘THOUGHTS OF A COLORED MAN’ on Broadway earlier this month
Her carefully curated luxurious lifestyle is, after all, hardly troubled by social turmoil or struggle.
There are chauffeurs to transport her between her magnificent homes in Manhattan and Long Island, celebrity dinner parties and tennis matches with close friend Roger Federer.
For years, this same privilege has been carried over into the office, where former employees claimed she prioritised staff who were ‘rich, white and thin’, while she ‘sidelined and tokenised women of colour, especially black women’.
Diversity, they added, was considered simply a matter of ‘optics’.
In the past year, under Wintour’s watch, the optics have been dreadful.
The incoming editor of Teen Vogue, Alexi McCammond, resigned over racist and homophobic tweets, while Adam Rapoport, editor of the group’s food magazine Bon Appetit, also stepped down after pictures emerged of him ‘blacking up’ as a Puerto Rican man in fancy dress.
Along with the accolades Wintour has gathered – including a damehood in 2017 – and current roles as artistic director of Vogue’s parent company Conde Nast, editor-in-chief at American Vogue and ‘global content adviser’ to the whole publishing group – there now nestles a coveted new title.
Few could have guessed it – least of all her disgruntled former employees – but Wintour is now head of a Diversity And Inclusion Council at Conde Nast.
On Tuesday Wintour (pictured with Jaden Michael) attended the premiere of the Netflix series Colin In Black And White, the story of BLM activist and American football player Colin Kaepernick
Wintour and Enninful. There are rumours that British Vogue’s editor-in-chief could be in line to take over from Wintour
In which case, she has presumably undertaken Conde Nast’s compulsory diversity awareness course.
If so, it’s definitely paying off.
Just last week she was accused of going on a ‘woke tirade’ and bowing to ‘American wokeness’ by stripping the word ‘Paris’ from the title of the French edition of Vogue to make the magazine sound less elitist, sparking a huge row.
She declared herself ‘horrified’ after attending a party to celebrate the magazine’s 100th birthday last month because a century’s worth of Vogue covers on display were overwhelmingly white.
On Tuesday she attended the premiere of the Netflix series Colin In Black And White, the story of BLM activist and American football player Colin Kaepernick, who ‘invented’ taking a knee before games in protest against police brutality against blacks.
A few days earlier, she was spotted at Thoughts Of A Colored Man, a Broadway show which uses ‘slam poetry’ to recount the ‘inner voices’ of black men in Brooklyn.
What is still unclear, however, is whether this is a genuine attempt to redress the balance, or – far more likely, some say – that Wintour simply accepts that woke is the new black.
And that the price of maintaining her remarkable power and influence is to do what she ‘has to do’ – a policy that has served her well for the past half-century.
For in the here-today, gone-tomorrow world of fashion, Wintour’s survival skills are the stuff of legend and part of her extraordinary fascination.
Mind you, there are plenty who feel that this latest transformation is a stretch too far.
‘She has overseen the Bon Appetit crisis, the George Floyd crisis and the Teen Vogue crisis, and that’s the title she gets?’ one source said.
‘Everyone was thinking, ‘What the f***?’ Why does she get to be in charge of everything? Even this? How is this person telling us to be more diverse?’
Times are certainly changing at Conde Nast, which also owns Tatler and Vanity Fair.
Magazine sales and advertising revenues have plummeted during the pandemic, while the Black Lives Matter movement has built momentum, challenging the role that fashion magazines have played in perpetuating what some claim are white ideals.
Today, Edward Enninful is at the helm of British Vogue – the first black man to hold the position – with rumours swirling that he could be in line to take over from Wintour.
Some have asked if her latest political manoeuvring is simply a knee-jerk reaction to safeguard her legacy.
‘Edward Enninful lives and breathes this stuff, he’s always putting diverse perspectives in throughout UK Vogue and has been doing so for four years,’ an insider said.
‘He wants different voices in the magazine, there’s a feeling that his view on diversity is authentic – on some level he has always felt different.
Wintour at a dinner hosted by British Vogue and Tiffany & Co with Naomi Campbell, Claire Foy and Idris Elba last month
Wintour was born in London in 1949. Her father was a newspaper editor and her family is linked to aristocracy
‘Anna’s perspective seems to some to be reactionary and somewhat inauthentic by comparison, like she’s protecting her legacy.
‘Edward is pursuing an activist, woke agenda which has made him an online superstar, and Anna, being Anna, has quickly caught on.’
Or as an insider with a rather different perspective puts it: ‘Edward’s appointment has certainly helped Conde Nast tick a very large box.’
No wonder Enninful, 49, and Wintour have a healthy respect for each other. An insider said: ‘They get on well. Anna has a lot of time for Edward but she’s also determined to cling on to power at all cost.’
Even if riding the woke tiger brings dangers of its own, particularly for a woman whose lifestyle might seem to be the very epitome of white privilege.
Born in London in 1949, her father was a newspaper editor and her family linked to aristocracy – she is related to the 18th Century novelist Lady Elizabeth Foster, who became the Duchess of Devonshire.
She moved to New York in her 20s – returning for a stint to edit British Vogue – and quickly rose through the ranks thanks to ‘Uncle Si’, media baron Si Newhouse, whose family has owned Conde Nast and Vogue since the 1950s.
If Si liked you, it is said, he paid for everything.
Spending most of her time in her Manhattan home, a four-storey townhouse in Greenwich Village, Wintour also has a sprawling holiday home on Long Island’s waterfront.
She opens up the 40-acre estate to friends – including actors Damian Lewis and Benedict Cumberbatch – and family every summer.
But the same razor-sharp attention to detail which brought her success – and that impeccable bob – is now focused on diversity.
Already a notorious workaholic who starts her day at 5am and regularly calls colleagues at 11pm after a working dinner, Wintour is ‘full on’ when it comes to diversity.
‘It’s become her new obsession,’ said a source.
‘Everything is seen through a prism of political correctness. She’s on every Zoom call, in every meeting.
This is a 71-year-old woman who you would have thought might be thinking of slowing down. But she’s driving herself harder than ever.’
Wintour was the main cheerleader for the appointment of Radhika Jones as editor of Vanity Fair magazine, a Vogue stablemate, replacing ‘old, white’ editor Graydon Carter.
She has also installed black editors at Teen Vogue and Bon Appetit magazines.
Sources suggest she’s taking regular advice from her 34-year-old daughter, Bee.
‘They are very close,’ one said. ‘Bee is offering her mother wise counsel and Anna is listening.’
Dame Anna’s inner circle might also be playing its part. Wintour has been photographed enjoying romantic meals in London, Rome and Paris with 71-year-old Love Actually star Bill Nighy, although both have remained tight-lipped about their friendship.
Nighy has not waded into recent woke debates, but has previously spoken of his pride that several of his films have covered important political issues such as the gender pay gap and gay rights.
For some, the recent decisions being made in Conde Nast’s stable of magazines under Wintour’s watchful eye have gone too far.
The decision to ‘rebrand’ Vogue Paris – which will now come under the oversight of Enninful, recently promoted to ‘European editorial director’ – was condemned as an onslaught on French tradition and culture.
In an editorial, Le Figaro blasted ‘the imposition of an Anglo-Saxon editorial line which can be summed up mainly by the issues of diversity and inclusivity’.
Out went 54-year-old Emmanuelle Alt as editor, and in came ‘young and hip’ 30-something Eugenie Trochu, who explained the change of name: ‘From Paris to Marseille, from Lille to Strasbourg, our identity is not born from a single place, and Vogue represents the best of emerging talents and voices.’
Wintour decreed the change to be effective immediately, starting with the November cover, which will feature rising black French starlet, Aya Nakamura.
One writer who has worked for Wintour has questioned the sudden and rather astonishing changes.
‘Anna had years to bring on black writers, models, photographers. Yet all of her moves to promote diversity and inclusion have largely happened since the Black Lives Matter movement burst into public consciousness in 2020. Until then, Vogue was white-centric.
‘A lot of people believe she is simply bowing to the pressure of online influencers and social activism movements like BLM and #MeToo and that this is all about her image.
Several black writers who have worked under Wintour – none of whom wanted to be identified for fear of retribution – told the New York Times they viewed her embrace of diversity as a calculated play.
‘It’s commendable she is taking action now but it all feels rushed, as if she’s seeking to protect her legacy as one of the all-time greats of fashion, which she undoubtedly is.
‘Why didn’t she champion inclusion much earlier on?’
Several black writers who have worked under Wintour – none of whom wanted to be identified for fear of retribution – told the New York Times they viewed her embrace of diversity as a calculated play.
‘Fashion is bitchy,’ one former black staff member told the newspaper.
‘At Vogue, when we’d evaluate a shoot or a look, we’d say ‘That’s Vogue’ or ‘That’s not Vogue’ and what that really meant was ‘thin, rich, white’.’
Moreover, the black staff members claim, they even assumed ‘white’ personas and spoke and dressed differently in their desire to fit into ‘Wintour’s world’ – a world that, professionally speaking, has now been blasted apart.
Wintour’s newfound willingness to embrace change was on full display during French Fashion Week this month.
When one fashion house relegated Trochu to the third row – fashion Siberia – Wintour calmly stood up from her seat in the front row and changed places.
‘That is something she would never, ever have done in the past,’ said one Los Angeles-based fashion buyer.
‘She is also demanding advertisers use more diverse models. Every fashion shoot has to have at least one model of colour.’
Diversity training has become mandatory across Vogue titles and the Conde Nast website has an entire section devoted to the company’s inclusion policies.
‘Ever since BLM, we’ve had to have regular training sessions over Zoom,’ one man said.
‘We have Zoom calls with experts in subject like unconscious bias. There are rumours Anna has been having one-on-one counselling on how to lead from the front.’
But some say the restructuring of the company is, ultimately, all about money and creating a global digital brand.
The editors of Vogue China, Germany and Italy have all gone to be replaced by ‘heads of content’.
A source said: ‘They’ve decided they want a brand for the digital age and Anna has been given global oversight of all the different editions.
‘Several of the more traditional fashion houses have privately been complaining about the direction Vogue has taken but they are like sheep and keep advertising.’
Wintour’s latest ‘obsession’ is said to be landing 18-year-old tennis champion Emma Raducanu for the cover of American Vogue.
‘To Anna, Emma is perfect,’ a source said.
‘She’s stunning, bi-racial and a perfect role model.
‘We’re going through a period of transition, but Anna is still very firmly at the helm. She will survive. She always does. She’s never going to cancel herself.’