He was educated at the Sedgwick Institute in Great Barrington, and learned the basics of painting from his father, Lemuel Maynard Wiles (1826–1905), 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. In his early years, he worked as an illustrator for American magazines, and later he devoted himself with great success to portraiture. He was a member of the Society of American Artists, which prefaced his 1897 election into the National Academy of Design as an associate. Wiles was also a member of the American Water Color Society. In his heyday—the first quarter of the twentieth century—Irving Wiles was one of the most successful portrait painters in the United States. Born in Utica, New York, he first studied with his father, Lemuel Maynard Wiles, who enjoyed a modest success as a landscape painter. Wiles then attended the Art Students League in New York City, where his teacher was William Merritt Chase. During a sojourn in Paris, Wiles then studied at the Académie Julian and also with the portrait painter Carolus-Duran (who was John Singer Sargent's teacher). Returning to New York in 1884, Wiles maintained a studio and also taught painting at the Art Students League and the Chase School, in addition to drawing illustrations for magazines such as Harper's and Scribner's. He catapulted to art stardom in 1902 when his portrait of the famous actress Julia Marlowe was exhibited at the National Academy of Design. Lauded for his dazzling brushwork and ability to capture the likeness of the subject, Wiles became the artist of choice for a socially prominent clientele, as well as important businessmen and political figures. Among his sitters were William Jennings Bryan and Theodore Roosevelt. In 1915 Wiles was awarded a gold medal at the Panama Pacific Exposition. He continued to exhibit and win awards for his work during the next several decades, but by the time of his death in 1948 his style of painting and the elegant subjects he portrayed had been supplanted by a radically different American art.