A freelance fashion photographer who lives in London, Bailey has been under contract to Vogue since 1960. His images have also appeared in such publications as Sunday Times, Daily Telegraph, Elle and Glamour. Michelangelo Antonioni's film Blow-Up was reportedly based loosely on Bailey's life.
Bailey made the films Andy Warhol (1973) and Beaton by Bailey (1971).
At one time he was married to French actress Catherine Deneuve.