Richard Florsheim was a painfully shy child, channelling all his energies into straight-A scholarship and crude, gloomy art. His father reluctantly helped him get an art education in Europe during the 1930s, but before World War II Florsheim managed to sell just one picture. There he was assistant director of the Arts Center Association, 1951-52, and taught at the Layton School of Art in Milwaukee from 1949 to 1950, and the Contemporary Art Workshop in Chicago from 1952 to 1963. From 1965 to 1973, he was a board member of the Illinois Arts Council.

He studied at the University of Chicago. Florsheim became a member of the National Academy of Design, the Society of American Graphic Artists, the Provincetown Art Association, which he served as Trustee and Vice President from 1962 to 1971, and the Chicago Society of Artists from 1947.