Philpot was a co-founder of the National Portrait Society. As a gay man he sometimes felt a need to be away from the constraints of British society and travelled widely through the 1920s, in Europe, America and North Africa. In Pittsburgh he met Matisse, a fellow juror on the Carnegie International Exhibition which awarded the prize to Picasso. He developed an overtly Modernist style that led the Scotsman newspaper to declare "Philpot goes Picasso!" His art fuses Symbolist elongated figures with an Expressionist angularity, as seen in this portrait.