He was born in Chicago to Henry Hobart Taylor and Adelaide Chatfield Taylor in 1865 as Hobart Taylor, but appended the "Chatfield" to his surname as the stipulation of a large inheritance from his maternal uncle Wayne Chatfield (making his full name Hobart Chatfield Chatfield-Taylor). He graduated from Cornell University in 1886, and in 1890 married Rose Farwell, daughter of former United States Senator Charles B. Farwell. His wife's portrait was painted by the Swiss-born American society painter Adolfo Müller-Ury, three quarter-length in 1893 (exhibited at Knoedler's New York Gallery in February 1894), and half-length drawing on a pair of white gloves in 1894 (exhibited at Knoedler's New York Gallery in January 1895); both are unlocated.
He edited a literary journal called America for a few years, and also served as consul to Spain in Chicago. He published his first novel, With Edge Tools, in 1891. His wife Rose died in 1918, and he married Estelle Barbour Stillman in 1920.
He had three sons (Wayne, Robert, and Otis), and one daughter, Adelaide Chatfield-Taylor Sohier. Wayne Chatfield-Taylor served as Under Secretary of Commerce and Assistant Secretary of the Treasury under President Franklin D. Roosevelt.
Books published by Chatfield-Taylor include:
- With Edge Tools (1891)
- An American Peeress (1893)
- Two Women and a Fool (1895)
- The Land of the Castanet: Spanish Sketches (1896)
- The Vice of Fools (1897)
- The Idle Born (1900)
- The Crimson Wing (1902)
- Molière: a biography (1906)
- Fame's Pathway (1909)
- Goldoni : a biography (1913) (on Carlo Goldoni)
- Chicago (1917)
- Cities of Many Men (1925)
- Tawny Spain (1927)
- Charmed Circles (1935)
- (17 January 1945). H.C. Chatfield-Taylor; Author, Authority on Moliere, Dies in California at 80, The New York Times
- Dole, Nathan Haskell. The Bibliophile Dictionary: A Biographical Record of the Great Authors, p. 125 (1904)
- (17 April 1909) Fame's Pathway, The New York Times ("Mr. H.C. Chatfield-Taylor is known by several novels, and furthermore, by a biography of Moliere which revealed a good deal of painstaking research.")
- Goldoni: A biography (full text online) (1913 publication date in this volume; some sources will state book was published in 1914)