In 1998 he had a cameo part in Love Is the Devil: Study for a Portrait of Francis Bacon as a young David Hockney.

[citation needed] Bowles has a large personal collection of designer clothing, including pieces by John Galliano, Mainbocher and Charles Frederick Worth.

[4] He served as a creative consultant for an exhibition at the MET featuring the iconic fashion worn by Jacqueline Kennedy Onassis during her White House years.

In October 2022, then aged 59, Bowles suffered an acute ischemic stroke while inspecting a home renovation, with catastrophic deficits in the areas of locomotion, speech, memory, and motor reflexes.

"...Blood flow to my brain was blocked," he writes in his narrative of recovery, published in British Vogue.