A painter and art critic, Pène du Bois trained at the New York School of Art under William Merritt Chase, Robert Henri, J. Carroll Beckwith, Frank Du Mond, and Miller from 1899 to 1905. As monitor for Henri's classs in these years, important one's in Henri's development, Pène du Bois (or Pennie, as his friends called him) became thoroughly imbued with Henri's realism.
In April 1905, Pène de Bois accompanied his father, a writer and music critic for the New York American, to Europe. In Paris, Pène de Bois frequented the galleries of the American Art Association and befriended the cartoonist and illustrator Demetrius Galanis. He studied briefly with Steinlein and exhibited at the Salon in 1905. In July, 1906, his father became ill and died on the trip back to New York.
Subsequently, Pène du Bois got a job as a reporter for the New York American where he remained for seven years, the last three of which he was art and music critic. He was not a good reporter, but his assignments at the Tenderloin Police Station in the theatre district and his opera assignments provided him with subject matter for his paintings. IN 1912, he joined the Association of American Painters and Sculptors and served on the Publicity Committee for the Armory Show. His major contribution was a special issue of Arts and Decoration which was devoted to the exhibition. He continued as editor of that magazine for seven years. He also worked one year at the New York Tribune as assistant to Royal Cortissoz and two years as art critic for the New York Evening Post. He taught at the Art Students League (1920-24, 1930-32, 1935-36) and at the Grand Central School of Art. He maintained a home in Westport, Connecticut, during this period.
From 1924-30, Pène du Bois lived in Garnes, France, where he devoted himself full-time to painting. Upon his return to New York he published monographs on John Sloan, William Glackens, Edward Hopper, and Ernest Lawson. In 1932, he founded a summer art school in Stonington, Connecticut, which continued sporatically until 1952. From 1941 to 1945, he worked on a book "Apes and Angels in Art," which was never published. He spent 1952-56 in France, then settled in Boston. His New York dealer was John Kraushaar.