Shaw was described as a “wealthy man-about-town, poet and minor novelist” before he began to paint seriously when he was in his 30s. His parents died when he was young, and he was raised by an uncle.
He graduated from Yale University and then studied at the Art Students League with Thomas Hart Benton. He also took private lessons from George Luks.
He served in World War I and during much of the 1920s, lived in Europe, writing articles for the New Yorker and Smart Set. Shortly after, he turned to abstract painting and exhibited in important avant-garde shows.
Michael Zellman, 300 Years of American Art