Anna Wintour cut a glum figure Thursday as she was pictured for the first time since news broke that she had split from her long term partner Shelby Bryan after 20 years together.
The longtime Vogue editor, 70, was spotted clutching a stack of papers while walking through the streets of New York City.
She hid her face behind her signature sunglasses but they didn't conceal her downcast, unsmiling expression.
Her outing came hours after it was first reported that Wintour and Bryan, 74, had parted ways.
The news marks the latest in a string of woes for the woman dubbed 'Nuclear Wintour' in recent months after her former friend released a scathing memoir and she was forced to admit to race-related 'mistakes' at Vogue.
Anna Wintour cut a glum figure Thursday as she was pictured for the first time since news broke that she had split with her partner Shelby Bryan after 20 years together
The longtime Vogue editor, 70, was spotted clutching a stack of papers out walking through the streets of New York City
Wintour was dressed in a long brown patterned dress, red boots and had a floral jacket slung over her arm.
She was holding her phone, wallet, a tablet and some documents in her right hand.
Page Six reported Wednesday that the relationship between the Vogue editor and Texas-born investor Bryan, 74, has been cooling since 2013 and the couple have only rarely been seen in public together since.
The powerful pair began dating back in 1999, with their romance causing a stir among New York's elite because Bryan reportedly walked out on his wife to be with Wintour.
At the time, the media maven had herself just divorced her psychiatrist husband David Shaffer, with whom she shares two children.
But Wintour and Bryan have rarely been seen in public in recent years.
She was dressed in a long patterned dress, red boots and her signature sunglasses as she appeared downcast and didn't smile
Her outing came hours after it was first reported that Wintour and Bryan, 74, had parted ways
Wintour hid her face behind her signature sunglasses and appeared downcast
The fashionista is known to have a wide circle of males friends, including the British actor Bill Nighy, who she has been regularly spotted with him at fashion shows and restaurant trips.
When Nighy was asked about the nature of their relationship in 2015, he replied, 'I obviously have nothing to say about that. There are a lot of rumors about me and probably about Anna Wintour’.
The separation sets up the prospect of a multi-million dollar break up, with Wintour boasting an estimated net worth of $35million alongside her husband's sizeable fortune.
The couple split their time between a $11.4m townhouse in Manhattan's trendy Greenwich Village and a sprawling holiday home in the Hamptons, which features a tennis court and stunning landscaped grounds leading down to the waterfront.
Anna Wintour and her partner Shelby Bryan have split after 20 years together, according to a Wednesday report running in Page Six. The couple are pictured together in 2016
Wintour and Bryan are pictured together in 2001
A representative for Wintour declined to comment on Page Six's report of her break up.
The site claims that there has been 'chatter around town that Bryan had gone back to his ex-wife Katherine, whom he left for Wintour more than two decades ago'.
However, an anonymous source stated that those rumors are untrue.
'Katherine and Shelby have kids together[and] are friends. That's all,' the insider alleged.
Wintour and Bryan's relationship is said to have run into trouble in 2013, when it was revealed that he owed $1.2 million in back taxes to the IRS.
The pair were often pictured at social events and tennis matches in the years prior, but have less frequently been spotted out in the time since.
According to Page Six, their relationship ran into trouble in 2013 and the pair began to be seen in public less frequently. They are pictured during a rare appearance together at the 2018 US Open
Anna Wintour's 19th century townhouse, in an exclusive block in Greenwich Village, New York, is estimated to be worth $11.4m, according to Zillow
Wintour is known to have a wide circle of males friends, including the British actor Bill Nighy, who she has been regularly spotted with him at fashion shows and restaurant trips. They are pictured together in Paris in January
Wintour and Bryan have largely kept their relationship private, but a 2007 Observer article gave a glimpse.
The US Vogue editor - who took the helm of the fashion bible back in 1988 - is famous for her icy persona. However, a source told the Observer that Bryan had 'softened' her.
'She smiles now and has been seen to laugh,' a source told that publication.
Wintour and Bryan do not have children together.
Wintour is a mother to son, Charles, 35, and daughter, Bea, 33, from her marriage to David Shaffer. They were married from 1984 until 1999.
Wintour was previously married to David Shaffer from 1984 until 1999. They are pictured together in 1989
Wintour does not have children with Bryan. She shares two children from her former marriage to Shaffer, including daughter Bea. They are pictured together last year
Wednesday's news of their separation comes amid a torrid year for the magazine titan.
In May, Wintour's former confidante, André Leon Talley, painted a scathing portrait of her in his memoir, The Chiffon Trenches back in May.
Talley, who worked at Vogue for more than two decades and eventually became the magazine's editor-at-large, slammed Wintour in his memoir, The Chiffon Trenches.
In one book passage, Talley described being frozen out by Wintour because he was 'too old, too overweight, too uncool' for her.
He went on to claim that there were an 'endless' list of writers, stylists and models who she has cast onto a 'frayed and tattered heap during her powerful rule'.
In another scorching paragraph he wrote: 'She is immune to anyone other than the powerful and famous people who populate the pages of Vogue.
'She has mercilessly made her best friends people who are the highest in their chosen fields.
'Serena Williams, Roger Federer, Mr. and Mrs. George Clooney are, to her, friends. I am no longer of value to her'.
Wintour has already endured a difficult year, with her fractious relationship with her former colleague and confidante André Leon Talley hitting headlines in May. Pictured: The former friends at the Met gala in 1999
The following month, Vogue's publisher Condé Nast was rocked by allegations of widespread racism.
As well as being editor of Vogue, Wintour also serves as the publisher's artistic director.
The claims prompted Wintour to issue a rare mea culpa, in which she apologized for race-related 'mistakes'.
In an internal memo to staff at Condé, Wintour admitted to letting 'hurtful and intolerant behavior' go unchecked during her 32-year reign at the fashion magazine, as well as not doing enough to champion black staffers and designers.
'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 ,' Wintour wrote.
'We have made mistakes too, publishing images or stories that have been hurtful or intolerant. I take full responsibility for those mistakes.'
In June, the influential editor made a rare mea culpa amid accusations of racism at Vogue's publisher Condé Nast
The note was sent out to staffers three days before Adam Rapoport, the editor-in-chief of another Condé Nast publication, Bon Appetit, resigned from his post after a photo surfaced of him in brownface, exacerbating a race-based controversy regarding pay equity in the outlet's video department.
Many believed Wintour may finally step down from her role as editor-in-chief of Vogue, but the company strongly expressed its support for their most famous employee.
However, her memo still appeared to indicate changing power dynamics and a possible loss of influence for an editor who was once deemed untouchable.
Wintour and Bryan are pictured in 2007. Her horror year appears to indicate changing power dynamics and a possible loss of influence for an editor who was once deemed untouchable