Rudenstine graduated with an A.B. in English from Princeton University in 1956 after completing a senior thesis titled "The Burden of Poetry: A Study in the Art of John Keats, Matthew Arnold and Thomas Stearns Eliot." While a student at Princeton, Rudenstine participated in Army R.O.T.C. After serving in the U.S. Army as an artillery officer, he attended New College, University of Oxford, on a Rhodes Scholarship and earned an M.A. In 1964, Rudenstine received a Ph.D. in English literature from Harvard; his dissertation, entitled "Sir Philip Sidney: The Styles of Love" and directed by Douglas Bush, treated Sidney's poetic development.