But although Matthews, a hedge fund manager and former racing car driver, may seem to lead a charmed, it has emerged that his family has been rocked by tragedy.
James' young brother, Michael, then 22, vanished in 1999 while climbing Mount Everest in the “death zone” region, above 8,000 metres. His body has never been found.
In his 2014 autobiography Confessions of a Chelsea Boy, youngest brother Spencer Matthews wrote about the family’s struggle after Michael’s death.
“His loss was devastating for the family and over time this became worse because the circumstances surrounding Michael's death have never been fully explained,” wrote Spencer, who starred in the reality-TV series Made in Chelsea. “James took the news badly. With just a year and a half between them, he and Mike were the closest of friends. The loss was heartbreaking for James.”
Today, James and Pippa take on gruelling physical challenges to raise money for the Michael Matthews Foundation, which builds schools in poverty-stricken locations around the world.