After graduating from the Slade, Shephard taught at Raynes Park County School whilst painting at night and often in pubs and music halls.
[3] In the spring of 1945, WAAC offered Shephard a full-time contract with the Ministry of War Transport, which he completed with a number of scenes painted in London.
[5] In 1942, Shephard had married his first wife, the daughter of a British businessman based in South Africa and in 1948 the couple moved to Cape Town with their children.
[7] Shephard continued to paint portraits and exhibition pieces but failing eyesight ended his career in 1990 and two years later he died of cancer in London.
[9] Shephard's painting Portrait of Mrs Marie Lydia Grant was burned by demonstrators during the Rhodes Must Fall protests at the University of Cape Town, UCT, in February 2016.