Born in Brunswick, Georgia, to a working, middle class family, Dawson attended Booker T. Washington’s famed Tuskegee Institute. After two years of studying drafting with architect, Dawson left Tuskegee for New York in 1907, where he became the first African American to be admitted to the Art Students League.
With money earned in the summer of 1912 from working in a Pullman buffet club car, Dawson was able to fulfill his dream of attending the Art Institute of Chicago. Dawson threw himself into student organizations such as the Art Students League of Chicago, and was a founding member of the Arts and Letters Society, which was the first black artists collective in Chicago.
After graduating from the School of the Art Institute in 1917, only weeks after the U.S. entered World War I, Dawson was accepted for officer training in the segregated armed forces.
Dawson returned to a changed Chicago. Tensions between the growing black community and a white working-class in search of jobs after the war resulted in the Race Riot of 1919. At the same time, blacks in Chicago were beginning to gain economic and political power with the Harlem Renascence and the “New Negro Movement.”
Dawson continued to pursue work as a fine artist. With other alumni of the Art Institute,he established the black exhibiting group the Chicago Art League in 1924, which was an important manifestation of the “New Negro Movement” in the visual arts.