Dine studied at the Boston Museum of Fine Arts School and at Ohio University. His early work consists primarily of images on canvas, to which three-dimensional objects (e.g., articles of clothing, garden tools) are attached. His “Shoes Walking on My Brain” (1960), for example, is a childlike painting of a face with a pair of leather shoes fixed to the forehead. His reputation was secured during the 1960s by his wittily incongruous painted images of tools, clothes, and other utilitarian and household objects. Dine's work of the 1970s pursued the same subject matter but showed a growing preoccupation with graphic media. His exploitation of nuances of line and texture is especially evident in his images of flowers and portraits of his wife done in the late 1970s. Dine also illustrated or coauthored several books.