The unknown sitter wears the long raincoat nowadays known as the ‘DR’ coat, introduced from March 1942, and also the fibre and rubber crash helmet which was widely replaced in July 1943 by a steel helmet. The despatch riders of the Royal Corps of Signals fulfilled a vital role during the Second World War (1939–1945) in maintaining communications, often under extremely difficult conditions, such as during the evacuation of British troops from Dunkirk in May and June 1940, when they often had to force their way through roads clogged with heavy traffic and abandoned vehicles.

From 1940 to 1944, Alfred Thomson was an Official War Artist to the RAF and painted bomber crews and patients in RAF hospitals. However, his sitters were not restricted to airmen and in 1941 he painted Miss Charity Bick, another despatch rider who was also the youngest woman Civil Defence worker to be decorated with the George Medal.