Anna Wintour, 70, dumped partner Shelby Bryan because she got 'bored'

EXCLUSIVE: ‘Anna dumped Shelby because she got bored, just as she gets bored with the length of skirts.’ Anna Wintour, 70, split with partner Shelby Bryan for the same reason she left her first husband, as friends say Vogue ‘takes precedence over all’

  • Anna Wintour’s split with her partner Shelby Bryan was reported last week
  • The Vogue boss had met the telecommunications businessman in 1997 while still married to her first husband Dr. David Shaffer, sparking a hot affair
  • A source close to Wintour said: ‘Anna is one of the world’s great flirts, and the previously twice-married Shelby was a skirt-chaser extraordinaire’
  • ‘Not surprisingly, they fell for each other the moment they locked eyes. Shelby was the Marlboro Man to David’s Pillsbury Doughboy,’ they added 
  • But their relationship ended because the 70-year-old grew bored
  • One confidante said: ‘Anna dumped Shelby, just like she dumped David – because she just gets bored with relationships, no matter how intimate’
  • Another said: ‘The relationship became strained for Shelby who found it difficult to deal with her driven style and ambition… whose life revolves around Vogue’
  • ‘They were going in different directions. The thing with Shelby is a repeat of what ended it with David – Anna gets bored, and her career takes precedence over all’ 

Jerry Oppenheimer is the author of the bestselling biography of Anna Wintour, FRONT ROW: The Cool Life and Hot Times of Vogue’s Editor In Chief, and biographies about the Kennedys, Clintons, Hiltons, Kardashians and other notables.

In the late 1990s, married Vogue magazine editor in chief Anna Wintour — dubbed ‘Nuclear Wintour’ by long-tyrannized fashion magazine colleagues because of her coldness — began a hot, clandestine affair with a handsome Texas businessman, Shelby Bryan, twice married with four children.

A friend who was aware of Anna’s liaison candidly compared her mild-mannered husband of 14 years, Dr. David Shaffer, father of their two children, who was a decade Anna’s senior, to the handsome, rugged new man in Anna’s life, declaring, ‘Shelby was the Marlboro Man to David’s Pillsbury Doughboy.’

As the longtime confidante observed, ‘Anna is one of the world’s great flirts, and the previously twice-married Shelby was a skirt-chaser extraordinaire. Not surprisingly, they fell for each other the moment they locked eyes.’

Shaffer, from England like Anna, had previously been married to an exotic, trendy Londoner who was years younger, Serena Bass. 

When Shaffer, long divorced, heard rumors that Anna was having a dalliance with Bryan, a dashing telecommunications entrepreneur just three years her senior, her much older, cuckolded husband was hoping to try to save his marriage. 

Barely communicating, and often spotted ‘fighting bitterly’ in an Italian restaurant near their super chic furnished, Greenwich Village home, the troubled couple flew off together to the romantic island of St. Barth’s, with Shaffer hoping to rekindle their marriage.

But the island’s erotic Caribbean sun felt more like the bleak midnight sun to Anna’s husband. As an observer who was eyewitness to the couple’s failed getaway told me, ‘They sat together on the beach but never spoke a word. David looked incredibly sad — and Anna was clearly just utterly bored.’

FIRST HUSBAND: Anna Wintour’s split with Shelby Bryan was reported last week. The Vogue boss had met Bryan while still married to her first husband Dr. David Shaffer (pictured together), sparking a hot affair. Sources close to Wintour said her most recent relationship ended over the same reason as her first marriage – she had grown bored

SPLIT: One close confidante said: ‘From what I know, Anna dumped Shelby, just like she dumped David – because she just gets bored with relationships, no matter how intimate, just as she gets bored with the length of skirts, or photographers who had served their purpose.’ Pictured: Wintour and Bryan in 2014

Wintour ‘was the one who ended’ her once steamy, two-decades relationship with Bryan. The two had met at a glitzy New York City Ballet gala at Lincoln Center in late 1997

Today, Anna Wintour’s live-in relationship with Shelby Bryan, 74, with whom she had replaced David Shaffer, now 84, is over, too.

‘Because she had grown bored again,’ a close source told me, Anna, who will celebrate her 71st birthday next month, ‘was the one who ended’ her once steamy, two-decades relationship with Bryan. The two had met at a glitzy New York City Ballet gala at Lincoln Center in late 1997.

Jerry Oppenheimer is a New York Times bestselling author. One of his 13 books is a headline-making, bestselling unauthorized biography entitled FRONT ROW: Anna Wintour, The Cool Life and Hot Times of Vogue’s Editor in Chief 

One close confidante told me, ‘From what I know, Anna dumped Shelby, just like she dumped David – because she just gets bored with relationships, no matter how intimate, just as she gets bored with the length of skirts, or photographers who had served their purpose, or assistants who didn’t act slavish enough, or designers who no longer turn on her fashion juices,’ as I documented with dozens of candid, on-the-record interviews with her friends, colleagues and associates in my biography of Anna Wintour, FRONT ROW: The Cool Life and Hot Times of Vogue’s Editor in Chief.

As news swirled in gossip columns last week about the Wintour-Bryan split, another well-connected source told me: ‘It’s no surprise Anna dumped him. She gets bored with people quickly and I believe that’s why she ended it with Shelby. 

‘But there are always two sides to every love story, and the relationship with Anna became strained for Shelby who found it difficult to deal with her driven style and ambition, a woman whose life revolves around Vogue, the world’s fashion Bible that she dominates with an iron hand in a velvet glove.’

The source continued: ‘Anna and Shelby haven’t actually really been together for a number of years, but kept their apparent split low profile, because they were going in different directions. The thing with Shelby is a repeat of what ended it with David – Anna gets bored, and her career takes precedence over all.’ 

While Anna has grown bored with the many men in her life – she began seeing older, prominent men even when she was just a teenager in London in the swinging ’60s – the one thing she has never tired of is her timeless, Louise Brooks bob hairdo, which she has been wearing since she was fourteen.

She modeled it after a cute reporter, Maureen Cleave, at the London Evening Standard newspaper of which her father, Charles Wintour, was the powerful editor. As a longtime family friend told me for my book, ‘Anna’s decision to copy Cleave’s hairstyle was psychologically complex’ because her father adored Cleave, and Anna idolized her father.

‘It’s quite complicated. But I’m sure Anna wanted to be able to say, ‘Look at me, Daddy, I look like Maureen. Anna always desperately sought her father’s love and attention, and he wasn’t always there to give it.’

Anna, of course, followed in her father’s footsteps as a journalist, but also in her private life; Charles Wintour was a notorious philanderer. He and Anna’s mother, Eleanor Trego Wintour, known as Nonie, a Bostonian, ended in divorce.

With media speculation surrounding her split with Bryan, Anna has declined comment through her spokesperson at Vogue. Shelby Bryan did not respond to my detailed telephone message left on Saturday. Also not responding to my phone message was his wife from his second marriage, as there have been media reports that they might have reconciled, which is doubtful. Bryan has two children with her, and two with his first wife. Anna is the mother of two with Shaffer.

Wintour modeled her iconic bob after reporter Maureen Cleave (pictured), who worked at the London Evening Standard newspaper of which her father, Charles Wintour, was the powerful editor

Beyond her failed marital life, Anna’s career at Vogue and Conde Nast has been in absolute turmoil, and appears in jeopardy. With circulation and advertising down, she’s also become a target of racism charges by young blacks –ranging from editors to writers and photographers who work for Vogue, and who claim that since she’s been editor in chief since 1988, they haven’t gotten their due.

The controversy was raised again on Saturday in The New York Times under the headline, ‘The White Issue: Has Anna Wintour’s Diversity Push Come Too Late?’

The lengthy story was published just as Vogue’s 316- page September issue, Headlined, ‘Hope,’ appeared, featuring, for the first time for Vogue, a majority of blacks – models, artists, photographers.

Last June, Anna sent an internal email in response to charges made against her by black staffers and freelancers. In it, she stated that she knew that the magazine ‘has not found enough ways to elevate and give space to’ black writers and journalists.’

And she admitted to have made ‘mistakes…publishing images or stories that have been hurtful or intolerant. I take full responsibility for those mistakes.’

But black staffers who have worked with her called her apology hypocritical. Some saw the all-black September issue as little more than a questionable attempt to change things racially at the magazine.

The Times story said that those interviewed asserted that racism at the fashion bible was ‘usually subtle, but sometimes blunt.’

From my dozens and dozens of interviews for my book detailing all aspects of Anna Wintour’s life, from her childhood in London to her dominance over the Vogue brand, I found no evidence of any racism on her part.

In fact, one of my anecdotes involved Anna’s close relationship with the late black Jamaican ganja-smoking reggae star, Bob Marley. 

Wintour is known to have a wide circle of male friends, including the British actor Bill Nighy, who she has been regularly spotted with at fashion shows and restaurants. They are pictured together in Paris in January

One of Anna Wintour’s first fashion magazine jobs was with Harper’s Bazaar in the mid-1970s, as a $12,500-a-year junior fashion editor, where she soon turned off her American colleagues with her British frost and in-your-face ambition.

It was during that time that she had fallen for the dreadlocked Rastafarian, the first Third World superstar, who was introduced to her by Chris Blackwell, founder of Island Records, a multimillionaire who had brought reggae into the mainstream, including Bob Marley & The Wailers.

And when Marley and his group came to New York for a concert Blackwell arranged for Anna to meet them.

As friends of hers at the magazine told me, Anna virtually disappeared for a week. As one said of her and Marley, ‘Anna met God.’

Marley took her off the scope during the Marley gig.

‘She went every night and stood backstage,’ making the scene with the legendary Marley who was a notorious womanizer.

As one of her friends told me, ‘Anna was riveted, and she’d go out every night after the concerts with the band to have dinner, go on the town.

‘When she came back we said, ‘Anna, you look exhausted.’ She had these purple circles under her eyes. She denied she had an affair, but she had this revelation and felt she had a mystical experience.

‘I said, ‘How come I’m not being invited?’ But then Anna found something THAT good, she wanted to keep it to herself. I don’t think anything moved her as much as Bob Marley.’

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