Irving Wiles was born in Utica, New York, and grew up in New York City. He received his first art instruction from his father, the landscape painter Lemuel M. Wiles. From 1879 to 1881 Wiles studied at the Art Students League, New York, under William Merritt Chase and J. Carroll Beckwith. At Beckwith’s urging, Wiles went to Paris in 1882, where he enrolled at the Académie Julian. He studied in the atelier of Charles-Émile-Auguste Duran, known as Carolus-Duran, a leading Parisian society portraitist who also taught John Singer Sargent. Wiles returned to New York in 1884 and launched his professional career with a series of commissions to illustrate articles for Century Magazine, Harper’s, and Scribner’s. By the mid 1890s he was able to give up illustration work and give his undivided attention to painting. In 1886 Wiles was elected to membership in the Society of American Artists, and in 1897 was elected to the National Academy of Design.
In 1887, shortly after his marriage, Wiles had moved into a studio in Manhattan at 103 West 55th Street, where he remained until 1908. During that period he taught during the winter at the Art Students League and the Chase School in New York, and summers at his Long Island studio in Peconic. Wiles, in the manner of many American artists before, including Chase, continued to travel in Europe on pilgrimages to see the art of the old masters first hand. In 1904 he went to Holland, and in 1905 to Spain, making the requisite tour of the paintings of Frans Hals and Diego Velázquez in the course of the two visits.
Although Wiles was best known during his lifetime for his portraits, he also executed figure studies, landscapes, and seascapes of a more informal nature. These latter works reveal the continuing influence of William Merritt Chase in their fluid brushwork and vibrant palette. In 1895, Wiles established a studio and summer school on the North Shore of Long Island in Peconic, across the bay from Shinnecock Hills, the site of Chase’s famous summer school and beloved home. By 1900 Wiles had built a his own cottage and studio. As time passed Wiles’ life revolved increasingly around his family and leisure activities at Peconic.