A well-noted supporter of African American artists, particularly those of the Harlem Renaissance era, Bennett settled in New York at an early age. Some her earliest notoriety came when Bennett placed first in an elementary school-wide art contest. She went on to study fine arts at Columbia University’s Pratt Institute. In the early to mid 1920’s Bennett was afforded an opportunity to study fine arts at the Academy Julian in Paris and philosophy at the Sorbonne. She developed as a graphic artist during this time and was proficient in a variety of mediums including watercolor and oils.

While she was in Europe, Bennett found herself in a community of other American expatriate artists. She was, however, one of the few Black American women living in France during her stay in Paris. Seemingly homesick, Bennett reportedly asked friends to send her books by Harlem Renaissance writers. In turn, she offered to smuggle James Joyce’s (censored) novel Ulysses when she came back to New York. Shortly after her return, Bennett was named assistant editor of Opportunity magazine. Her column, “The Ebony Flute,” highlighted various literary activities of Harlem Renaissance luminaries such as Langston Hughes and Countee Cullen. Bennett also continued to publish her own work. “To Usward,” which paid homage to Jessie Redmon Fauset’s 1924 novel, "There is Confusion," was one of Bennett’s best known poems.

Bennett, who was much sought after when her career opportunities burgeoned, also served as assistant professor in the Art Department at Howard University. From 1937 to 1941, she fellow artists and activists such as Romare Bearden, Aaron Douglas, Norman Lewis, Augusta Savage, were members of the Harlem Artists Guild. Bennett also directed the Harlem Community Art Center and helped establish the George Washington Carver Community School in New York. She and her husband Dr. Albert Joseph Jackson, one of her fellow instructors at Howard University, left New York and settled for a time in Florida. However, struct by the racism that they encountered in the “Sunshine State,” the two eventually left Florida and established a residence on Long Island, New York. By the time of Jackson’s death in 1936, the once thriving community of Harlem was transitioning. Crippled by the fallout from the Great Depression and other challenging conditions, Harlem Renaissance artists sought new outlets for their work. Bennett found a measure of respite by working as for the Federal Writers Project and the Federal Art Project.

She also married a second time—to fellow writer and educator Richard Crosscup, who was white. Their blissfulness was soon disrupted when position as director of the Art Center was rescinded. She was targeted by the House Un-American Activities Committee (H.U.A.C.) under suspicion of being a Communist--an accusation that was unfounded.

Bennett’s later years were spent as a secretary at the Consumers Union. After retiring, she and her husband settled in Kutztown, Pennsylvania. “Poet, artist, short story writer, columnist, journalist, editor, educator, administrator… Gwendolyn Bennett was a true Renaissance woman. Her vision of community building between diverse groups and her commitment to developing the race was instrumental to the Harlem community during and after the Harlem Renaissance and left a legacy for future writers and artists.”

The recent confirmation of two of Bennett’s works, in the hands of private collectors, excited the arts community and avid admirers of the artist hope that other images will be found.