Arriving in 1925, Douglas quickly became immersed Harlem’s cultural life. He contributed illustrations to Opportunity, the National Urban League’s magazine, and to The Crisis, put out by the National Association for the Advancement Colored People. Douglas created powerful images of African-American life and struggles and won awards for the work he created for these publications, ultimately receiving a commission to illustrate an anthology of philosopher Alain LeRoy Locke’s work, entitled The New Negro.

Douglas had a unique artistic style that fused his interests in modernism and African art. A student of German-born painter Winold Reiss, he incorporated parts of Art Deco along with elements of Egyptian wall paintings in his work. Many of his figures appeared as bold silhouettes.