Druitt was educated at Winchester College, where he won a scholarship at the age of 13, and excelled at sports, especially cricket and fives. He was active in the school's debating society, an interest that might have spawned his desire to become a barrister. In debates, he spoke in favour of French republicanism, compulsory military service, and the resignation of Benjamin Disraeli, and against the Ottoman Empire, the influence of Otto von Bismarck, and the conduct of the government in the Tichborne case. He defended William Wordsworth as "a bulwark of Protestantism", and condemned the execution of King Charles I as "a most dastardly murder that will always attach to England's fair name as a blot". In a light-hearted debate, he spoke against the proposition that bondage to fashion is a social evil.