Called "the queen of the bohemian artists", Abercrombie was involved in the Chicago jazz scene and was friends with musicians such as Dizzy Gillespie, Charlie Parker, and Sarah Vaughan, whose music inspired her own creative work.

[2] Her parents, Tom and Lula Janes Abercrombie, were traveling opera singers who happened to be in Austin on the day of Gertrude's birth.

[5] The following summer she made her first sale at an outdoor art fair in Chicago and received an honorable mention in the newspaper for the event.

[3] Within Abercrombie's avant-garde social circle she was the inspiration for the song "Gertrude's Bounce" by Richie Powell, who claimed that she walked "just like the way the rhythm sounds in the Introduction",[6] and she appeared as herself in James Purdy's Gertrude of Stony Island Avenue and as a fictional character in Purdy's Malcolm, Eustace Chisholm.

[3] Abercrombie painted many variations of her favored subjects: sparsely furnished interiors, barren landscapes, self-portraits, and still-lifes.

Many of her compositions feature a lone woman in a flowing gown, often depicted with attributes of sorcery: an owl, a black cat, a crystal ball, or a broomstick.

[8] Tall and sharp-featured, she considered herself ugly;[9] in life she sometimes wore a pointed velvet hat to accentuate her witch-like appearance, "enjoy[ing] the power this artifice gave her over others who would fear or recoil from her".

[4]Her work evolved into incorporating her love for jazz music, inspired by parties and jam sessions she hosted in her Hyde Park home.

Musicians such as Sonny Rollins, Max Roach, Jackie Cain, and the Modern Jazz Quartet were considered friends.