Willey was educated at University College School, Hampstead before coming up to Peterhouse, Cambridge, where he had won a scholarship in 1915. He was commissioned into the West Yorkshire Regiment soon after and he eventually graduated in 1921 with a first in History and English. He married Zélie Murlis Ricks (1900-1988) in 1923. He became a fellow of Pembroke College in 1935. He was appointed King Edward VII Professor of English Literature in 1946. He was elected a Fellow of the British Academy in 1947. He served as President of Pembroke from 1958 to 1964. He retired from his position as King Edward VII Professor of English Literature in 1965. He died in 1978.