Terry O'Neill was born in the East End of London in 1938 and enjoyed early success as a jazz musician before undertaking National Service then joining the Daily Sketch as a news photographer (1960-63). From 1963 he worked for titles including Vogue, Paris Match and Rolling Stone as a fashion and portrait photographer and is often considered a peer of other 'Swinging London' working-class photographers including David Bailey, Terence Donovan and Brian Duffy.

This image captures the model Jean Shrimpton walking barefoot in a London street c.1965. Shrimpton was the first model to become a fashion leader in her own right, capturing public attention and causing some controversy after she was photographed at Melbourne Racecourse in December 1965 watching the Australian Gold Cup in an above the knee skirt of similar length to the one shown here. In his landmark book on the 1960s fashion, art and pop scene 'Revolt into Style' (1970) George Melly identified her as the prototype of the 'Dolly Bird', the new youthful icon of fashionability.

The photograph is also notable for its sense of informality and movement, a characteristic device of O'Neill and his generation.