Illustrator and writer born the son of a publican in St. Albans. He studied painting at Kingston College of Art, Byam Shaw School of Art and St. Martin's School of Art. Artist Partners represented him and he worked as a copyrighter, photographer, and art editor. Bailey also worked as an author and wrote more than twenty books on various subjects. He spent several years in New York working as a writer and an illustrator for Time and Life. He continued to paint throughout his career. His illustrative work included covers for Vogue and Homes & Gardens.

The portrait depicted is of Fiona Macpherson (1940-2000), whom Bailey married in 1976. After the birth of their first child, she devoted herself to family life. She returned to full-time work after being offered the editorship of ‘Harpers & Queen’ in 1994. Her portrait is in the National Gallery of Scotland. She worked until weeks before her death from cancer in 2000.