The Women of Brewster Place, Naylor’s first novel, won the National Book Award in 1983. Employing what critic Kathryn Palumbo calls “female-defined imaging,” the novel presents a circumscribed and circumscribing world from the perspective of several women, although one woman, Mattie, seems to exercise some control over the characters and over the narrative itself. The interconnecting stories foreshadow Naylor’s larger structural concerns, as Naylor’s novels themselves seem to be interconnected. Kiswana is from Linden Hills, the title of Naylor’s second novel, about an African American neighborhood where middle-class people have sold themselves out to pursue the American Dream. Naylor’s treatment of these two African American neighborhoods, so close geographically and so distant attitudinally, is unusual.

Several scholars have cited the many ties between The Women of Brewster Place and Ann Petry’s The Street (1946), and in her emphasis on setting, Naylor resembles Toni Morrison. Besides the literary influences, there are political and cultural influences reflected in Naylor’s work. In the years before the publication of The Women of Brewster Place, African Americans responded to patriarchal society’s devaluation of women by affirming female virtues and the central position of women in their communities; in the years before the publication of Linden Hills (1985), social historians depicted the rise of an African American middle class. Naylor’s novels reflect literary trends, contemporary social concerns, and changing racial attitudes.