This article argues that for Virginia Woolf, racial alterity or the trope of race operates as a grounding for imagining androgynous subjectivity. In doing this, I will first sketch out how the author’s preoccupation with the question of race came into contact with the gender issues that she saw as important to address in order to tackle the oppressive, masculinist literary climate of early twentieth-century England. I will then turn to examine how Woolf’s construction of race as a prerequisite for androgyneity is ultimately an impossible task, by a close reading of Orlando: A Biography, specifically, the title character Orlando’s relationships with the unnamed dead Moor, his Russian lover, Sasha, and the Turkish gypsy named Rustum, respectively. Although the concept of androgyneity, as many Woolf critics contend, was intended by Woolf as a means to authorize herself as an aspiring woman writer, a rendering of race as a prerequisite for androgyneity is a task doomed to fail, precisely because identity itself is the contentious space where its normalized and subversive repetitions form and deform each other in constant conflict and negotiation with one another, almost always risking the reinforcement of gender binarism and normative sexuality.