Alston shared studio space with Henry Bannarn at 306 W. 141st Street, which served as an open space for artists, photographers, musicians, writers and the like. Other artists held studio space at "306", such as Jacob Lawrence, Addison Bate and his brother Leon. During this time Alston founded the Harlem Artists Guild with Savage and Elba Lightfoot to work toward equality in WPA art programs in New York. During the early years of 306, Alston focused on mastering portraiture. His early works such as "Portrait of a Man" (1929) show Alston's detailed and realistic style depicted through pastels and charcoals, inspired by the style of Winold Reiss. In his "Girl in a Red Dress" (1934) and "The Blue Shirt" (1935), Alston used modern and innovative techniques for his portraits of young individuals in Harlem. "Blue Shirt" is thought to be a portrait of Jacob Lawrence. During this time he also created "Man Seated with Travel Bag" (c. 1938–40), showing the seedy and bleak environment, contrasting with work like the racially charged "Vaudeville" (c. 1930) and its caricature style of a man in blackface.