He was educated at Street Peter"s School, York and Trinity College, Cambridge where in 1894 he obtained a First Class in Classical Tripos and the Walker Prize in Classics.
He was also briefly a British Liberal Party politician. He emigrated to Australia in the 1890s. They had one daughter.
Jessie died in 1913.
They had one son. Naylor was a Lecturer and tutor at Ormond College, University of Melbourne, from 1895–1906. He was Vice-Master of Ormond, from 1903-1906.
In 1913 he was appointed Vice-President of the British Classical Association. He was Governor of the Public Library of South Australia.
He was Professor of Classics in the University of Adelaide, South Australia.
He was Chairman of the Scotch College, Adelaide. In 1927, Naylor decided to return to Britain and settled in Cumberland. In 1926 he had been selected as Liberal prospective candidate for the Whitehaven division of Cumberland.
lieutenant was a Unionist/Labour marginal offering little hope of success for a Liberal.
He contested the 1929 General Election and finished a poor third. He did not stand for parliament again.
He was elected a Governor of Keswick School. He remained in Cumberland, and died in Cockermouth in 1945.
They shared a particular interest in internationalism and were both active in the League of Nations Union.
He was a member of the Adelaide University Council. He was a member of the Council of Street Mark’s College (University).