Born in England in 1931 of Irish immigrant parents and raised in Liverpool. He was educated at Oxford University, where he graduated in 1953 with First Class Honours in the Honours School of Modern History. Awarded a Goldsmiths' Company's Commonwealth Traveling Research Scholarship, he spent the next two years studying Latin Palaeography and the history of Medieval Philosophy at the Pontifical Institute of Mediaeval Studies in Toronto.[1]
Oakley's graduate studies were interrupted by the need to return to England to serve for two years (followed by reserve duty) in the British Army, where he rose to the rank of lieutenant in the Royal Corps of Signals and was attached to the Commonwealth Communications Army Network (COMCAN). Having decided to return to North America, he completed his Ph.D. in History at Yale University in 1959 and spent the next two years teaching in the Yale History Department before taking a position in the history department of Williams College. There, for forty years, he taught medieval and early-modern history, as well as courses in the Interdepartmental History of Ideas major (of which he was co-founder) and in the Environmental Studies Program until his retirement in 2002.
Oakley spent seventeen years of senior administrative service at Williams (1977–94), first as Dean of the Faculty, then as President of the College, and later, 2002–03, as President of the American Council of Learned Societies in New York City—an interim appointment.
He is married to the former Claire-Ann Lamenzo of Manchester, CT, a fiber artist and horsewoman. They have four children—Deirdre, Christopher, Timothy, and Brian—and seven grandchildren; William, Charlotte, Ryann, Erin, Kevin and Joslyn Oakley.[citation needed]