 Oakley was born on 28 September 1968 in Shrewsbury and was educated at Shrewsbury School, where he was awarded a Rank Foundation Leadership Award, and King's College London, before going to St Stephen's House, Oxford, where he studied for ordination in the Church of England.He was ordained a deacon (1993) and a priest (1994) by David Hope.Oakley served as assistant curate of St John's Wood Church from 1993 to 1996.