Born in Orangeville, Ontario, Skelton attended Queen's University and was a professor there from 1907 until 1924, publishing in that time many books and articles on Canadian history, economics and politics. He left Queen's to join the young Department of External Affairs which he organized on an enduring basis, thereby making his most significant contribution to Canada. Skelton advised three prime ministers, Meighen, King and Bennett, on foreign policy, advocating an independent Canadian position distinct from that of Britain.