During his peak, he was one of the leading portraitists in America,[1] working alongside his compatriots John White Alexander and Cecilia Beaux to paint the American leisure class.

[3] He was educated at the Sedgwick Institute in Great Barrington, and learned the basics of painting from his father, Lemuel M. Wiles (1826–1905[4]), who focused primarily on landscapes.

From 1879 to 1881 he studied in the Art Students League of New York under James Carroll Beckwith and William Merritt Chase, and later in Paris under Carolus-Duran.

[5] While active as a varied painter in the late 19th century, his career reached new heights in 1902, when his portrait of the actress Julia Marlowe was exhibited at the National Academy.

[9] Toward the end of his career Wiles was noted for the plein-air land and seascapes he painted at his home in Peconic, New York.