[1] She came to prominence in the 1980s and 1990s with photo-text installations such as Guarded Conditions and Square Deal that questioned the nature of identity, gender, race, history and representation.

[2] Simpson continues to explore these themes in relation to memory and history using photography, film, video, painting, drawing, audio, and sculpture.

[10] Here she developed her signature style of combining text with studio-like portraiture, while questioning if documentary photography was factual or served as a constructed truth generated by photographer themselves.

[23] In a 2017 issue of Vogue Magazine, Simpson showcased a series of portraits of 18 professional creative women who hold art central to their lives.

[29] Simpson's work often portrays black women combined with text to express contemporary society's relationship with race, ethnicity and sex.

In many of her earlier works, the subjects are photographed with obscured faces, causing a denial of gaze and the interaction associated with visual exchange.

Simpson's use of "turned-back figures" was used to not only "refuse the gaze" but to also "to deny any presumed access to the sitter's personality, and to refute both the classificatory drives and emotional projections typically satisfied by photographic portraiture of black subjects.

"[30] It has also been suggested that these figures "stand for a generation's mode of looking and questioning photographic representation"[31] Through repetitive use of the same portrait combined with graphic text, Simpson's "anti-portraits" have a sense of scientific classification, addressing the cultural associations of black bodies.

"[31] Simpson's 1989 work, Necklines, shows two circular and identical photographs of a black woman's mouth, chin, neck, and collar bone.

The white text, "ring, surround, lasso, noose, eye, areola, halo, cuffs, collar, loop", individual words on black plaques, imply menace, binding or worse.

The final phrase, text on red "feel the ground sliding from under you," openly suggests lynching, though the adjacent images remain serene, non-confrontational and elegant.

The women's faces are obscured by a white-colored oval shape each with one of the following letters inside: A, E, I, O, U. Underneath the corresponding portraits are the words: Amnesia, Error, Indifference, Omission, Uncivil.

[38]Many critics associate the work with the slave auction, as a reminder that black "enslaved women were removed from the circle of human suffering so that they might become circulating objects of sexual and pecuniary exchange.

Simpson juxtaposed found, pinup-style images of young African American women from 1957 with present day photographs of herself reproducing the model’s pose, clothing and backdrop.

[47][48] Simpson’s newer works have been series that incorporate found photographs and appropriated imagery from vintage magazines and the Associated Press.

Simpson’s newer work continues to thread figuration, abstraction, metaphor and paradox to challenge race and gender stereotypes.

[49][50][51] Artists that have influenced Simpson's work include David Hammons, Adrian Piper, and Felix-Gonzalex Torres; and writers like Ishmael Reed, Langston Hughes, Ntozake Shange, Alice Walker, and Toni Morrison because of their rhythmical voice.