Before he became Colonel Roberts, Herbert Harrington Roberts attended the Norwich School of Design, and later, the Royal Academy Schools, studying alongside Frederick Walker and William Blake Richmond, At his home in Thorpe, Roberts' studio was often occupied by Frederick Sandys, who, Roberts admits in his memoirs, "was not noted for prompt payments." When Sandys offered to buy some tapestries from Roberts, "I offered to take in exchange one of his beautiful female chalk heads, but not having one at the time that appealed to me, he suggested making a drawing of me, which I now have." Roberts quit Thorpe a year after this portrait was drawn, leaving behind his career as an artist for the 1st Warwickshire Militia.