The couple wed in 2004, but things have been icy between them as early as 2013. In fact, they have rarely been since in public together since. The marriage reportedly went sour after it emerged that Bryan owed $1.2 million in taxes to the IRS in 2013.
So, what happened between this elite couple? There have been suspicions that Bryan reunited with ex-wife Katherine Bryan. Katherine's husband, investment banker Damon Mezzacappa, passed away in 2015. Shelby left her for Wintour in the late '90s. However, an insider revealed this was not why Wintour and Shelby decided to part ways.
"Katherine and Shelby have kids together and are friends. That’s all," a source told Page Six.
The venture capitalist has reportedly been laying low in Texas.
For years, people have suspected that Wintour's close friendship with actor Bill Nighy might have been something more. When asked about the nature of their relationship in 2015, he said, "I obviously have nothing to say about that. There are a lot of rumors about me and probably about Anna Wintour." They were most recently spotted together in February, where Wintour was reportedly "beaming the whole time" while they had dinner.
Wintour and Shelby first got together in 1999, which was just as scandalous as their split is shaping up to be. Shelby allegedly left his fiancée at the time to be with Wintour, who had recently divorced psychiatrist David Shaffer.
Wintour is valued at $35 million, and her now-ex is extremely wealthy, too, so we can expect to see hefty divorce proceedings. The pair split their time between a $11.4 million townhouse in Manhattan and a luxury Hamptons holiday home. Wintour and Byran share no children together.
The split is another setback in an already difficult year for the Vogue editor. In May, her right-hand man, André Leon Talley, did not hold back in his memoir, The Chiffon Trenches.
"I have huge emotional and psychological scars from my relationship with this towering and influential woman," he wrote. "Not a day goes by when I do not think of Anna Wintour." He claimed that he was iced out because he was "too old, too overweight, and too uncool."
Then, the fashionista found herself in trouble again. In June, Vogue's publisher, Condé Nast, was accused of being biased and racist. Wintour penned an internal memo in which she apologized for "publishing images or stories that have been hurtful or intolerant."
"I want to say plainly that I know Vogue has no found enough ways to elevate ad give space to black editors, writers, photographers, designers and other creators," she said.