In the mid-1930s, Abercrombie moved out of her family home and became heavily involved in the local art scene. She was a painter for the Works Progress Administration from 1932 to 1940, where she became close with other artists and began building her “homegrown socialite” reputation. As a WPA painter, she made $96 a month; with her room costing only $11 a month, Abercrombie was able to focus all of her time on her art, becoming embedded in the creative community and cultivating her bohemian lifestyle.

Abercrombie was adored by every class of artist working in Chicago at that time and her salons, modeled after Gertrude Stein’s in Paris, were vital to the shaping of the Chicago arts scene. The famed Chicago writer Nelson Algren loved her work. Jam sessions were held on Sundays (with Abercrombie often playing piano) at her dilapidated mansion and Sonny Rollins, Dizzy Gillespie, Charlie Parker, Max Roach and other jazz luminaries passing through the city would be in attendance. Richie Powell even wrote “Gertrude’s Bounce” in reverence for Abercrombie’s lively gait and presence. Author James Purdy, who was a very close friend of hers, modeled the character Eloisa in his 1959 book Malcolm after her and later fictionalized the Chicago arts community and Abercrombie’s influence over it in 1997 in his final novel, Gertrude of Stony Island Avenue. Other friends and fans of Abercrombie included Studs Terkel (who interviewed her in 1977 on his WFMT radio show), Saul Bellow, Charles Sebree, Ivan Albright and Milwaukee artists Karl Priebe and Dudley Huppler.

Despite her reputation as the exuberant nexus point of the Chicago arts scene, Abercrombie’s work dealt with psychic landscapes, themes of isolation, occult imagery and her inner consciousness. Abercrombie’s first solo exhibition was held at the Chicago Society of Arts in 1934. Dizzy Gillespie once described her as “the first bop artist; Bop in the sense that she has taken the essence of [the] music and transported it to another art form.” Abercrombie was making rather unconventional paintings, filled with surrealist imagery, sparse, spooky spaces and reoccurring motifs of cats, owls, shells, moons, and floating doors. However, she was working within the conventional framework of painting interiors, still lifes, and self-portraits, just as the bop musicians were creating a completely new form of jazz by approaching jazz’s elemental components with an unconventional, avant-garde spirit. “They’re ‘off the beam,’ kind of goofy,” Abercrombie said of her paintings, “like the bop music.” Rather than the individual elements of the composition themselves being meaningful, they obliquely add up to a captivating, constructed tableau.

Abercrombie’s paintings often invited deciphering and psychoanalysis, and were executed with more intimacy than artists of the Surrealist movement, to which her work was often compared, even though Abercrombie didn’t see Magritte’s work until the early 1950s and did not closely follow the national and international arts scene. Abercrombie uses a very personal symbolic language, controlled style, and moody palette, creating enigmatic, dream-like scenes that chronicle her fears, obsessions, and the fragility that lurked beneath her gregarious and warm persona. “It is always myself that I paint,” Abercrombie once remarked. Studs Terkel, a close friend and a consummate American oral historian, described her paintings as “an extension of herself— original, unique, endearing and revealing.”

In 1977, the final year of her life, Abercrombie received a major retrospective at Hyde Park Art Center. For the last decade of her life, her health declined considerably, as did her creative output, and she was bedridden during her last few years, though still often received visitors. Abercrombie left a rich body of work, which is held in many public and private institutions, as dictated by her will that established the Gertrude Abercrombie Trust to donate her work to museums throughout the Midwest. The Illinois State Museum holds a large collection of her work and held a retrospective in 1991, and the Elmhurst Art Museum showed a recent celebration of Abercrombie in 2018.