[1][2] Dole studied English literature at Olivet College and later finished a degree in art history, apprenticing with George Rickey.
[2] Dole moved to Oakland, California in 1941 to study at Mills College and joined the United States Army Air Corps the following year, where he served until 1945.
[3] Dole worked briefly in the advertising industry before beginning graduate studies in art at University of California, Berkeley in 1946[2] and lecturing there in 1947.
[4] Dole's art was largely watercolor-based until he took a sabbatical in Florence, Italy in 1955, at which point he began to work in collage by incorporating Italian landscape elements.
[7] His work was considered influential in the Santa Barbara collage scene,[8] and was highly regarded by New York Times art critic John Russell.