This dissertation articulates how Ann Petry challenges the traditional notions about African American masculinities and redefines them with more positive and progressive attributes in her works. It probes the ways Petry’s black male characters face oppression, stereotypes, and systemic barriers, in relation to American hegemonic masculinity and (black) femininity. As black men, they are in the process of being permanently constructed due to the intersecting power of race, gender, class, and other categories on personal, social, and state levels in a context specific manner. I implement an intersectional reading method to analyze Petry’s constructions of African American masculinities, enhanced by a two-step strategy of identify-by-explaining categories and asking the other question about their constitutive and overlapping dynamics. This dissertation also addresses Petry’s underrepresented role in subverting the socially constructed and maintained stereotypes about African American masculinities and proposes two reasons for it. Firstly, there is an actual interplay between reinforcing and subverting stereotypes in Petry’s novels and short stories, which I regard as part of an evaluation of her oeuvre. On the one hand, she depicts stereotypical African American male characters in “Like a Winding Sheet” (1945), The Street (1946), and “In Darkness and Confusion” (1947) in order to revisit and refine the violent and sexually driven black masculine stereotypes. On the other, she represents black male characters as racially-conscious and diverse in “Solo on the Drums” (1947), The Narrows (1953), and “The New Mirror” (1965) to maintain her non-essentialist and progressive definitions of black masculinities. Secondly, reading Petry on the periphery of protest fiction – epitomized in the works of black male authors such as Richard Wright – overshadows her divergent aesthetics and impedes her contribution to the advancement of mid-century African American fiction. By depicting black male characters from the perspective of a female author, this dissertation showcases how Petry modifies the male-dominated modes of representation of black masculinities. The critique of Petry’s representations of African American masculinities, thus, expands outside the male vs. female dichotomy and repositions her beyond the confinements of protest novel aesthetics.