From 1896, when he was 11 years old, Taylor's family lived at Ormond.
In 1947, his wife, as Doris Taylor, was created a Dame Commander of the Order of the British Empire. (Herbert Taylor himself appears to have not been knighted or been on any Honours List, despite his accomplishments.)
In 1902, at the age of 17, Taylor left Caulfield Grammar School and began work as a clerk at a chemical manufacturer.
In 1913, Taylor became senior audit clerk with a Melbourne firm of accountants, Young & Outhwaite. He secured his permanent career with a partnership in 1917; he was to become senior partner on A. H. Outhwaite's retirement in 1947.
A founding (1928) fellow of the Institute of Chartered Accountants in Australia, from 1933 Taylor was one of two inaugural vice-presidents of the offshoot Australian Chartered Accountants Research Society of Victoria. Its object was to bring members of the institute together, 'professionally, socially and in various forms of sport'. Under the society's auspices, Taylor published two booklets, The Organisation of a Chartered Accountant's Office (1933) and The Audit of Sharebrokers' Accounts (1937).
Taylor joined the Institute of Public Affairs and was to serve on its council in 1945 - 1966. In 1944, as an I.P.A. nominee, he chaired several meetings of Victorian political groups opposed to the Australian Labor Party and reported the outcome to Robert Menzies. These meetings preceded Menzies' conventions — in Canberra in October and at Albury, in December — which led to the formation of the Liberal Party of Australia.
Taylor served on the Liberal Party's finance committee and became a trustee of the State branch. After two years as president of the Associated Chambers of Commerce of Australia, he voiced in April 1947 the Liberal stance against the rise of 'autocratic Socialism', deploring worker intimidation by an extremist minority of trade union leaders and calling on Australians to restore "the desire to do good work".
A councillor (1945-55) of the University of Melbourne, Taylor was chairman (1950-54) of its finance committee. In addition, he was treasurer (1950-55), vice-president (1956-61) and president (1961-65) of the Royal Automobile Club of Victoria. He became a fellow of the Institute of Directors, London. In 1959 he was appointed CMG.
During World War II, Taylor wrote a much-appreciated newsletter of club doings, spiced with 'salty humour' and a 'pinch of sentiment', for the eighty members on active service. By invitation, he joined the international Senior Golfers' Society and the Royal and Ancient Golf Club of St Andrews, Scotland. He also enjoyed fly-fishing, bowls and horse-racing.
Taylor's eldest son, Grahame, subsequently joined Young & Outhwaite.