There’s probably no one in the celebrity world who wouldn’t want to sit next to Anna Wintour at a fashion show. But it’s her personal life that many people are curious about. According to Closer Weekly, Wintour’s first marriage to her now-ex-husband David Shaffer ended in divorce in 1999 when it was revealed that she was having an affair with a married man. All the tabloid coverage wasn’t easy for the naturally shy Wintour, as she also wasn’t used to having her private life splashed across gossip headlines at the time. New York magazine revealed that she and businessman Shelby Bryan met in 1997 and had an illicit affair that ended both their marriages. With that said, Wintour did her best to ignore all of the tabloid noise the best she could. “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,” she told the publication.
And while the way her first marriage ended managed to raise a lot of eyebrows, the way her second marriage to Bryan ended certainly got plenty of people gossiping about it, too.