In his youth, Tomaso played the piano for a dance orchestra in which he met drummer Dean Cornwell, who also became a famous illustrator and an influence on Tomaso’s own style. Illustration historian Walt Reed wrote that Tomaso’s “work mostly resembled Cornwell’s in concept and broad brush style.”
John T. McCutcheon, a family friend and cartoonist for the Chicago Tribune, encouraged Tomaso’s artistic talent. Tomaso studied at the Art Institute of Chicago with J. Wellington Reynolds. He also studied at the Art Students League of New York with teachers including Dean Cornwell, Robert Henri and Harvey Dunn.