Bennett's main training was as a visual artist; she taught design, watercolor painting, and crafts at Howard University after graduating from Pratt in 1924; she also studied fine art in France. Starting in 1926, Bennett was hired as an assistant to the editor at Opportunity, and her graphic designs were often used in both that magazine and The Crisis. Bennett also published short stories in Fire!! (1926) and Ebony & Topaz (1927), and had a regular column on the arts in Harlem in Opportunity between 1926 and 1928.
After Bennett married Dr. Albert Joseph Jackson in 1927, the couple briefly moved to Florida, and Bennett's creative output slowed. She did later return to New York City and joined the Harlem Artists Guild. Unfortunately, though her poems were widely anthologized at the time, Bennett never published a complete book collecting poetry and short fiction. However, in 2018, a book called Heroine of the Harlem Renaissance: Gwendolyn Bennett's Selected Writings was published by Pennsylvania State University Press.