Katharine Esdaile was born to Andrew McDowall, secretary to the Girl’s Public Day School Trust, and his wife, Ada Benson, the first Headmistress of Norwich, Oxford and Bedford High Schools. She went to Notting Hill High School and Lady Margaret Hall, Oxford. At Oxford, she focused her interest on classics, fascinated by the study of antique sculpture. From 1904 onwards, Esdaile published articles in the Journal of Hellenic Studies and Numismatic Chronicle, primarily on Greek and Roman coins and on classical portrait sculpture.