﻿Anna Wintour has been the queen of Fashion for over three decades. While the chief
editor of Vogue has portrayed a cold-hard exterior to the public, behind closed doors,
Anna has had to juggle a turbulent personal life and an intense career. After recently confirming
the end of her two-decade relationship with Shelby Bryan, whispers of a possible budding romance with
Bill Nighy have started to stir. But this isn't the first time the fashion mogul's love life
has been the talk of the town. Back in the 1990s, her first marriage to David Shaffer ended in such
a scandal it was all anyone could talk about. Anna Wintour's first publicized romance was with
professor and child psychiatrist David Shaffer. Anna has been notorious for keeping her private
life out of the spotlight, so we don't know much about how she and David first met.
The couple got married in 1984 when Anna was thirty-four years old and
David was forty-eight. One year later, they welcomed their first child together,
a son they named Charles Shaffer. Two years after that, their daughter, Bee Shaffer, was born.
In 1988, Wintour became editor-in-chief of Vogue, crowning her as one of the most influential
women in Fashion. Anna put all of her energy into her career, and her hard work paid off.
It didn't take long for everyone to know her name - even if they knew nothing about Fashion.
As her career skyrocketed, it seemed as though Anna was perfectly capable of balancing her
work and home life. Wintour admitted to New York Magazine that juggling a family and her
career wasn't always easy, but she always did her best to combine the two worlds.
She explained, "Of course, there were times, particularly when you travel, when it's very
tough to leave the kids, particularly when they were very young. I would try to take them with me
when I could just so they could experience and see a little bit of what a workday involved."
After over a decade of marriage, she and her husband appeared to be going strong. However,
that was all going to change after she met Shelby Bryan.
The year was 1997, and Anna attended the Benefit Ball for the New York Ballet. Bryan, a millionaire
telecommunications tycoon, was seated next to her during the event, and their chemistry was
instantaneous. The pair couldn't help but notice the sparks that flew between them, but there
was one problem … They were both married. At the time, Shelby was married to his second
wife, Katherine Bryan, and the pair shared two sons. Before that, he had been married
to Lucia Bryan, and they had two daughters. Unable to resist one another, Anna and Bryan began
having a secret affair. For two years, the pair would meet in secret behind their spouses' backs
for steamy rendezvous. When news of their affair broke out in 1999, the tabloids went wild.
According to reports, Shelby's wife wasn't surprised about his secret romance with the
Vogue editor because she was already familiar with his habit of being unfaithful. However,
Anna's husband was left baffled and heartbroken. David learned about his wife's affair after he
heard a message Bryan had left for her on their answering machine. He felt "upset and
disturbed" by Wintour's betrayal. It wasn't as if Anna and Shelby had a one-night fling,
their affair had gone on for two years, and that wasn't something that David was able to forgive.
That same year, Wintour and Shaffer divorced, officially ending their fifteen-year marriage.
Meanwhile, Shelby told his wife Katherin he was leaving her for the Vogue editor,
putting an end to their marriage in 2001. While scandalous affairs normally
result in careers being on some shaky ground, that wasn't the case for Anna.
In fact, since Bryan had numerous political connections, their relationship opened a lot
more doors for the British Journalist. One source said at the time their affair
became public, "Shelby was this real Type-A player kind of guy, and he gave
her access to a whole different world." Wintour refused to address the media storm,
although she acknowledged that her career and life in the public eye
came with a heavy price to pay. During a New York Magazine profile
interview at the time, she said, "There are certain things that no one wants to
read about in the tabloid press. You know that your friends and your family have one vision,
and if the outside world has another, then that's just something that you just don't focus on."
Eventually, the drama over their now-not-so-secret romance settled down. Soon, the Vogue
editor-in-chief and telecoms tycoon became one of America's most powerful couples. It seemed like
a match made in heaven when it came to bridging the worlds of Fashion, business, and politics.
Following their stint in the media, Anna and Shelby preferred to keep their relationship
private. He occasionally arrived on her arm to events over the years, though they
were mostly photographed together at sporting events like Wintour's favorite, the US Open.
The couple kept things so low-key that no one really knew if they actually got married.
Numerous publications reported that the pair had tied the knot in 2004,
although the details are so few and far between that we can't be sure that it even happened.
After nearly ten years of being the ultimate power couple, their relationship reportedly
hit a rough patch in 2013 after Shelby's legal tax issues came to light. It was revealed that
the businessman owed $1.2 million in taxes to the IRS. Reports at the time also said
he had lost a great deal of his original $ 30 million fortune during the property recession.
Following Bryan's tax crisis, the couple's public appearances became even more of a rare occurrence.
As far as we can tell, the pair were last seen together at the 2018 US Open. Two years later,
Anna and Shelby confirmed that their relationship was over.
Although news broke of the former couple's split in 2020, it seems as though their
romance had fizzled out quite some time ago. An insider claimed that Shelby's trouble with
the IRS "was the beginning of the end," and Wintour felt like he had "become a liability."
A separate source for ET corroborated news of the split, adding that this "is not a new story" as
"they haven't been together for a while." Neither Wintour nor Bryan commented about
their breakup. Given how much they had both sacrificed to be together, the public was left
to speculate about what could have caused the end of their two-decade-long union.
There were rumors that Shelby might have rekindled things with his ex-wife, Katherine.
Meanwhile, whispers of a romance between the Vogue chief editor and
'Love Actually' actor Bill Nighy also began to stir.
It's no secret that Anna and Bill had a close friendship for over a decade. The public
first noticed the pair started enjoying each other's company in 2010. Over the years, they
were often spotted together at several events, dinners, fashion shows, and movie theaters.
Naturally, there were some that couldn't help but wonder if what the pair shared was more
than just friendly. In 2015, Nighy was asked about his relationship with Wintour and whether
there was more to it than met the eye. He responded, "Obviously, I have nothing
to say about that. There are a lot of rumors about me and probably about Anna Wintour."
Anna's confirmed split from Shelby only drew more attention to her closeness with Bill.
At the beginning of 2021, the pair were seen having dinner together at Sant Ambroeus in
New York City. According to an onlooker, Wintour was "beaming the whole time."
Just a few months later, they were spotted in Italy, having yet another cozy dinner date.
Bill arrived at the restaurant with roses that he had gifted to the fashion mogul.
The pair reportedly enjoyed each other's company as they chatted away through the night.
Anna and Bill have yet to confirm their romance, but they also haven't denied it. Does that mean
they couldn't be bothered to entertain baseless rumors? Or is it because they aren't ready to
share their true feelings for one another with the public? We'll leave that to you to decide.
Whatever the case may be, as the seventy-three-year queen of fashion
heads into the future as a single - or maybe not so single - woman, we hope she's happy.
Throughout her life, she's always held her head high,
proving to the world that there is nothing that will bring her down.