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Shepherd was described in The Times obituary (31 May 1948) as "a sensitive rather than a forcible painter of the figure, landscapes, interiors, and still-life subjects. His work was distinguished by good taste in feeling, colour and arrangement and virtuosity in execution." He was born in Stoke-under-Ham, Somerset and educated at Rugby and Corpus Christi College, Oxford. He studied art at the Slade School (1898-1901). In 1912 he joined the New English Art Club, acting as hon. secretary in 1939. He exhibited at the Royal Academy, the Goupil Gallery and elsewhere. His paintings include Interior of the Wren Library, Cambridge, The Music Room, Drawing Room Interior, The Children's merry-go-round, Chelsea. He was an associate member of the Societe Nationale des Beaux-Arts and a knight of the Order ofthe Crown of Belgium.