Bailey remembers that when he was growing up in the East End of London, he saw three alternatives for his future: to be a boxer, a trumpet player or a car thief. So he bought himself a trumpet and tried to play in the spirit of Chet Baker, but his trumpet was stolen in Singapore where he was doing his national service in the RAF. After losing this, Bailey became interested in photography and discovered the work of Henri Cartier Bresson. Inspired by these, Bailey bought a camera (a Rolleiflex copy, 6x6) in 1957. He soon realized that although one could be taught the techniques of photography, the ability to create images and imbue them with imagination comes from within oneself.
Like others in his generation, Bailey poured over Life Magazine. After finishing his national service in 1958, he got a job with David Olin, who was then the main supplier of photos to Queen Magazine. After that he became an assistant to the fashion photographer, John French, in London. In 1960 Bailey was 22 years old and already was working as a free lancer for British Vogue. His name quickly became as well known as the people he photographed: the fashion designer, Mary Quant, and everyone who was involved in Bazaar, on the King's Road, the photographer, Bill Brandt, and also the Beatles, the Rolling Stones, The Who and singers like Marianne Faithfull and Sandie Shaw. Other subjects included actresses such as Mia Farrow, Catherine Deneuve, Geraldine Chaplin, Sarah Miles, Jeanne Moreau, Julie Christie, Virginia McKenna and actors like Peter Sellers and Michael Caine. Bailey also photographed the period's current fashions on the streets of London or New York for magazines like American Vogue or Glamour. The Shrimp or Jean Shrimpton, Marisa Berenson, Penelope Tree and Twiggy were some of the models that came in front of his motor-driven camera eye. During the 1960s Bailey became Vogue's foremost photographer. On one occasion he said: I wanted to be like Fred Astaire, but I couldn´t, so instead I went for the next best thing, which was to be a fashion photographer.