Feiler completed his undergraduate degree at Yale University where he was a member of Ezra Stiles College, before spending time teaching English in Japan as part of the JET Program. This experience led to his first book, "Learning to Bow: Inside the Heart of Japan", a portrait of life in a small Japanese town. Upon his return he earned a master's degree in international relations from the University of Cambridge in the United Kingdom, which he chronicled in his book "Looking for Class".