Jim Flora was another jazz-associated visual artist. Irwin Chusid, “public editor” of Luskin’s Krugman Truth Squad is an author of a book collecting some of Flora’s work, some selections are posted here and here. I think you have to respect a writer equally comfortable with free market political commentary and jazz cultural history.
Flora’s work certainly has a great deal of charm, however I think his cult-standing is hurt by the fact that his art graced the covers of LPs for majors labels Columbia and RCA. On the other hand, David Stone Martin is known for his Verve covers and Francis Wolff’s photos helped make Blue Note a collector favorite. Unlike the majors, Blue Note and Verve specialized in jazz, and developed a consistent look through their cover designs.