- Famous London fashion photographer synonomous with the Swinging Sixties.
- The photographer in Blow-Up (1966) is loosely based on Bailey.
- His father was slashed by the Krays [East London gangsters] who Bailey later in his career would photograph.
- He was awarded the C.B.E. (Commander of the British Empire) in 2001.
- Suffers from Dyspraxia.
- In the mid-'60s he was developing a film project that would have been his directorial debut titled "The Assassination Of Mick Jagger" which was to be produced by his friend Roman Polanksi.
- Introduced to his future wife Catherine Deneuve by Roman Polanski. They married 2 weeks later and separated in 1967 after two years of marriage, but did not file for divorce until 1970.
- Lived with Jean Shrimpton from 1962 to 1965.
- His break came in 1960 when the Daily Express published his picture of the model Paulene Stone in a mini and a mohair sweater, crouching down amid a swirl of autumn leaves, playing with a squirrel.
- Dropped out of school at the age of 15.
- Served in the British Royal Air Force where he was stationed in the Far East.
- Wrote his memoir "Look Again" which was published in the UK in 2020.
- After finishing his military service he took an internship with the fashion & society photographer John French.
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