Woodley was born in Bristol, son of William Augustus Woodley, a solicitor, and the former Ada Constance Strachan. His paternal grandfather George Woodley was also a poet. Woodley was educated at Cheltenham College (1902–07) and University College, Oxford (matriculated 1907, BA 1910). During his time at Cheltenham, he was a member of the Clifton Rugby Football Club.
In World War I he served with the Royal Munster Fusiliers and was awarded the Military Cross) "for conspicuous gallantry". After the war, he taught English at several schools. He also worked at the Somerset County Gazette.