Portraits form a thread throughout Indiana’s work, from the self-portraits of his art school years to his powerful Mother and Father (1963–66). Indiana is most known, however, for the symbolic portraits he began painting in the early 1960s. In these he employs significant colors, shapes, numbers, and words to create homages to artists and literary figures such as Charles Demuth and Herman Melville, as well as portraits of family members and friends.
Red Sails is a symbolic portrait linked to his Mother and Father painting. Indiana began the painting after hearing a vagrant in Jeannette Park sing “Red Sails in the Sunset.” The incident brought back the memory of his father, Earl Clark, playing the song on the piano, upon which the song’s sheet music was kept. However, in his journal entry for August 3, 1963, Indiana recorded that the work was an "August painting" (the month his mother was born), and "very much in rememberance of Carmen [his mother]."
The painting also illustrates the many layers of meaning that are characteristic of Indiana’s work. The artist frequently incorporated personal references into his works, and Red Sails recalls not only his parents but the ships and daily life the artist knew from living on the Coenties Slip waterfront. Furthermore, Indiana identified strongly as an American painter, and the red, white, and blue color scheme can be read as an allusion to the American flag.