The truth about Anna Wintour's annus horribilis

Bethan Holt
·7-min read
anna wintour - John Shearer/Getty Images for THR
anna wintour - John Shearer/Getty Images for THR

Anna Wintour might have been hoping for a little more serenity in the first year of her 70s. When she celebrated her milestone birthday last November, after all, she was riding high – still the apparently untouchable queen of fashion and having just welcomed her second grandchild.

“She’s not just ageing gracefully, she’s ageing fashionably. She’s changing the whole game of who can wear what at what age,” one Vogue writer told American website Page Six.

She was also, we now know, settling into single life having split from her Texan millionaire partner, Shelby Bryan. As she prepares to mark her 71st birthday on November 3, Wintour will still be reeling from a tumultuous year – every queen must tough out their own annus horribilis and this has undoubtedly been Anna’s.

ANNA WINTOUR -  167356-5
ANNA WINTOUR - 167356-5

This week, news broke of her split from Bryan, 74 – a story that has bemused fashion insiders for whom their separation had already become common knowledge. Some outlets mistakenly reported that a mega divorce battle would ensue, but the couple – who met at a New York City Ballet gala in 1997 and were famous for their early public displays of affection – were never married and have been living increasingly separate lives for several years.

Says a source close to Wintour’s circle in New York: “They were always seen together at the tennis, they’d go to Paris for the French Open and the US Open. But then a few years ago, they stopped going. The tipping point was his tax scandal.”

Once one of Bill Clinton’s most generous donors, in 2013 Bryan was accused of owing the US government $1.2 million (£920,000 today) in taxes. Not long after, rumours began to swirl about Wintour’s possible romantic association with the actor, Bill Nighy.

anna wintour paul smith bill nighy - Getty Images
anna wintour paul smith bill nighy - Getty Images

Nevertheless, photos emerged this week of the famously pristine American Vogue editor-in-chief cutting a “glum figure” out and about in Manhattan, those famous Manolo Blahnik heels and impeccably fitted Prada or Chanel frocks swapped for comfortable boots and a long, loose dress.

In reality, this is just the latest storm that Wintour has faced this year: 2020 began with doubts about whether the Met Gala – the red-carpet fundraiser she organises every year – would go ahead due to the pandemic. It was ultimately cancelled.

Once lockdown hit, Wintour ensured she remained visible, regularly appearing on Vogue’s Instagram page in her quarantine uniform of knits and luxe tracksuit bottoms (a concession to athleisure, showing just how much had changed in mere weeks), and rallying the fashion industry by partnering with Tom Ford on A Common Thread, a fund to help struggling designers.

Andre Leon Talley anna wintour - Stephen Lock Retained
Andre Leon Talley anna wintour - Stephen Lock Retained

But then came Black Lives Matter and a racism row that looked like it would unseat Wintour from her Condé Nast throne. In the wake of George Floyd’s murder, former Vogue employees spoke publicly about their experiences at the magazine. Shelby Ivey Christie tweeted that her time as a media planner at US Vogue in 2016 was “the most challenging and miserable” of her career, adding that bullying from white colleagues was “exhausting”. There was mounting criticism, too, that Condé Nast, where Wintour is also artistic director, employed too few black people and rarely featured them in the magazines they publish.

Within days, Wintour’s reputation had transformed from fashion’s leading purveyor of Left-leaning liberalism (she was once rumoured to be in line to become America’s ambassador to the UK) to a baby boomer hopelessly out of touch with millennial and Gen-Z values.

But more than being a victim of woke culture, there seemed to be mounting evidence that Wintour had presided over a publication – and industry – which had, at best, ignored its systemic problems with race and at worst, actively discriminated against ethnic minorities. An apology went some way to making amends, but also fuelled suggestions that Wintour might be on the brink of resigning.

Anna Wintour and Edward Enninful arrive at The Fashion Awards 2019 - Getty Images Europe
Anna Wintour and Edward Enninful arrive at The Fashion Awards 2019 - Getty Images Europe

“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,” she wrote. “We have made mistakes, too, publishing images or stories that have been hurtful or intolerant. I take full responsibility for those mistakes.”

All unfortunately timed alongside the release of The Chiffon Trenches, the autobiography of Wintour’s most high-profile black employee, André Leon Talley, one-time creative director at Vogue. He called her a “colonial dame” in an interview to promote the book (a no‑holds barred kiss-and-tell of his time as one of Wintour’s closest friends), adding that “she is entitled and I do not think she will ever let anything get in the way of her white privilege”.

“She was really upset by André’s book and everyone close to her was upset for her,” says the New York insider, “She took it personally.” As the gossip mill reached fever pitch, Condé Nast CEO Roger Lynch gave her his backing and she was left to get on with the job of repairing its fractured reputation, recently appointing black British editor Chioma Nnadi as editor of Vogue.com.

“She’s been facing the rest of the Condé woes, they’ve had to lay people off and there was a lot of chatter that Edward Enninful [editor of British Vogue] would do American and British Vogue,” says the New Yorker. “She’s a product of her generation. There are a lot of people who are happy to see her come undone, there’s schadenfreude. But the people who are close to her say that she’s not as bad as you’d think. When she does go, it will be on her own terms.”

Indeed, it’s unfortunate that news of Wintour and Bryan’s separation has hit the news just when she would undoubtedly have preferred attention to be focused on her latest Vogue cover featuring Naomi Campbell. After telling Campbell, in an interview on her YouTube channel, that she had had to fight company executives to be allowed to feature her on the magazine in 1989, she has now made the supermodel the magazine’s fourth black cover star in a row (your virtue signalling alarm bells may ring here, but Vogue says that most of these were booked long before this summer). Leon Talley even appears to have changed his tune, writing on Instagram that: “both women [Wintour and Campbell] represent the better angels of today who address the importance of giving back to better mankind”.

And what of Wintour’s love life? There have been rumours – which appear to be unfounded – that Bryan may have reconciled with his first wife, Katherine, whom he left for Wintour over two decades ago after their affair became public. Wintour was then married to David Shaffer, with whom she has two grown-up children, Charles, 35, and Bee, 33.

Bee Shaffer Carrozzini anna wintour -  Â©Eddie Mulholland
Bee Shaffer Carrozzini anna wintour - ©Eddie Mulholland

In February, she was spotted dining with 70-year-old Love Actually star Bill in New York, where onlookers described her “beaming” and “looking happier than ever”. Could the British actor have melted her ice queen persona? “She’s definitely got a huge crush on Bill. She’s softer than you’d think,” says the source.

Whether true romance is on the cards remains to be seen, but it would certainly spell a more optimistic end to a year that has rocked Wintour’s reign to its core.

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