In 1959 he 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, he captured and helped create the 'Swinging London' of the 1960s: a culture of high fashion and celebrity chic. The three photographers socialised with actors, musicians and royalty, and found themselves elevated to celebrity status. Together, they were the first real celebrity photographers. The film
Blowup (1966), directed by Michelangelo Antonioni, concerns the work and sexual habits of a London fashion photographer played by David Hemmings and is largely based on Bailey.
The 'Swinging London' scene was aptly reflected in his
Box of Pin-Ups (1964): a box of poster-prints of 1960s celebrities and socialites including Terence Stamp, The Beatles, and notorious East End gangsters the Kray twins (see photo).
The box was an unusual and unique commercial release, and it reflected the changing status of the photographer that one could sell a collection of prints in this way. (The strong objection to the presence of the Krays on the part of fellow photographer Lord Snowdon was the major reason no American edition of the "Box" ever appeared, nor a British second edition issued.)
Of Supermodel Jean Shrimpton, Bailey said:
She was magic and the camera loved her too. In a way she was the cheapest model in the world - you only needed to shoot half a roll of film and then you had it. She had the knack of having her hand in the right place, she knew where the light was, she was just a natural.
As well as fashion photography, Bailey has been responsible for record album sleeve art, for performers including The Rolling Stones and Marianne Faithfull. He has also directed several television commercials and documentaries.
One of Bailey's most famous works depicts the Rolling Stones. It features Brian Jones, who drowned in 1969 while under the influence of drink and drugs. He is seen standing slightly apart from the rest of the group.
In 1976, Bailey published
Ritz Newspaper together with David Litchfield.
Bailey was awarded the CBE in 2001.
In 2005, he was involved in a feature titled "British Rule" for
GQ, charting the British influence on rock n' roll, photographing several artists including Paul Weller, Jarvis Cocker, Razorlight, Brian Eno, M.I.A., Ian Brown, The Futureheads, Belle & Sebastian, Damon Albarn, Dizzee Rascal, Kaiser Chiefs, Robyn Hitchcock, Super Furry Animals, and Colin Blunstone for the spread.
He maintains that his style of photography remains the same:
I've always tried to do pictures that don't date. I always go for simplicity.
He has worked with Manchester band Oasis, boxer Naseem Hamed and supermodel Naomi Campbell.