[3] Kestelman obtained a scholarship to the Central School of Art and Design in 1922, where his teachers included both A.S. Hartrick and Bernard Meninsky.
Hartricks' teaching led Kestelman to an appreciation of French art and he would visit France for extended periods most years from 1930 onwards.
Later he created sets for Carmen at Sadler's Wells in 1940 and for several productions by the Old Vic Company including the 1944 staging of Richard III starring Ralph Richardson, Sybil Thorndike and Laurence Olivier at the New Theatre.
[1][7] The publisher Noel Carrington commissioned Kestelman to produce a large series of pastel drawings for a book on the Bertram Mills Circus.
[3] During World War Two, Kestelman served as a full-time air-raid warden and also drew scenes of workers at an aircraft repair factory.