Born in Algona, Iowa, Cowles is best known as a landscape and figure painter. He graduated from Dartmouth College and studied art in Paris. Returning to the United States, he settled in New York, continuing his studies at the National Academy of Design and the Art Students League. He earned a fellowship to the American Academy in Rome and remained in Europe, primarily in Italy, for several years. During World War I he served in the Intelligence Department of the United States Navy. He spent much of the 1920s traveling through Japan, China, Egypt, Greece, and India. Beginning in the 1930s he split his time between New York City and Santa Fe, New Mexico, where he associated with other modern painters, including John Marin, Andrew Dasburg, Marsden Hartley, and B.J.O. Nordfeldt.
