Gaylor was a painter and arts organizer who worked in a mode that combines modernism, folk art, and documentary. As a young man he moved to New York City and took a job with Butterick Sewing Patterns that he retained for most of his career. He studied at the National Academy of Design. In 1912 Gaylor met and befriended Walt Kuhn, helping Kuhn to install the 1913 Armory Show. Gaylor exhibited two impressionist paintings in that ground-breaking show. Gaylor's associates included Isabel Bishop, Kenneth Hayes Miller, Reginald Marsh, and other younger artists associated with John Sloan and the Art Students League. He was one of the founders of the Penguin, an arts club that busied itself with costume balls, performances, murals, and design projects through the early 1920s. He collected folk art in Maine in the summers, and this influenced his style. In the 1940s, he moved to Long Island.
