Oakley is a noted teacher, historian and administrator. A native of Liverpool, England, he was educated at Oxford University, at the Pontifical Institute of Medieval Studies in Toronto, and at Yale University, where he completed a Ph.D. in medieval history before joining the Williams faculty in 1961.
In 1977, he was appointed dean of the faculty at Williams, a post that he held until being named president in 1985.
During his presidency, the college's endowment more than doubled, and the college's bicentennial year of 1993 saw the successful completion of a $173 million fund drive, the record for a liberal arts college.
Oakley has written extensively on medieval and early modern intellectual and religious history and on American higher education.
He also holds honorary degrees from Northwestern, Wesleyan, Amherst, Bowdoin, the former North Adams State College and Williams.