In 1959, Bailey became a photographic assistant at the John French studio, and in May 1960, he was a photographer for John Cole's Studio Five, before being contracted as a fashion photographer for British Vogue magazine later that year. He also undertook a large amount of freelance work.

Along with Terence Donovan and Brian Duffy, Bailey captured and helped create the 'Swinging London' of the 1960s: a culture of fashion and celebrity chic. The three photographers socialized with actors, musicians and royalty, and found themselves elevated to celebrity status. Together, they were the first real celebrity photographers, named by Norman Parkinson "the Black Trinity"