Bailey was born in Stapleford in 1901, the son of farmer John Bailey. He was educated at Coldicott School, Hitchin, Manor House School, Clapham, Grammar School Reigate, and Queen’s College, Taunton. He came to St John's College in 1919 to study Natural Sciences. In 1921 Bailey switched to study Law, and graduated LLB in 1923 with a 2.1. In 1922 he was called to the Bar and joined the staff of Messrs Gibson & Weldon. In 1926 Bailey moved to Aberystwyth to lecture at the University College of Wales, and from there moved to Birmingham University as Reader in English Law. He returned to Cambridge in 1931 to become a Fellow and College Lecturer at St John's. A University Lectureship followed in 1934, and then a Readership in Law in 1946. When H.A. Holland retired from the Rouse Ball Chair of English Law in 1950, Bailey was elected to succeed him, holding the post until 1968.
Bailey served his College as Director of Studies (1934-50) and Tutor (1939-46), and served the University as Senior Proctor (1936-7). Bailey wrote on legal history, editing the Cambridge Legal History Series, and on property law. His best known work, however, is his 'Law of Wills', first published in 1935. Bailey was a popular lecturer.
He was twice married and had one son, and died in 1980.
Obituary in The Eagle: Vol 69, Easter Term 1981, p. 29
Accessible online at: https://documents.joh.cam.ac.uk/public/Eagle/Eagle%20Volumes/1980s/Eagle_1981.pdf