Irving Ramsey Wiles traveled to Paris in 1882 to study under the instruction of Carolus-Duran, the teacher of other notable American artists including John Singer Sargent, Theodore Robinson and Kenyon Cox. Due to the influence of his teacher as well as his relationships with William Merritt Chase, John Singer Sargent and James Carroll Beckwith, Wiles' style developed from more academic works into one with bravura brushstrokes.
After the artist's return to New York, he earned a living painting illustrations for magazines such as Century, Harper's and Scribner's. Wiles also taught at the Art Students League, the Chase School (also known as the New York School of Art) and later in the studio at Little Peconic Bay near Shelter Island. It was his time on the eastern end of Long Island that Wiles created some of his most light-filled and Impressionistic pictures including Drying Sails, Shelter Island. The work displays his broad brushstrokes loaded with paint, creating a surface with a thick impasto of blues, greens and reds that convey a sense of the movement of the wind in the harbor, catching the sails.