This study examines the feministic elements of the major novels and essays by the early 20th century female writer Virginia Woolf, and the contemporary male South African writer J. M. Coetzee. There is an affinity between the two authors in that their works give us a depth of insight into imperialism, fascism, and patriarchy based on a dichotomous way of thinking. First of all, it is noteworthy that the elusiveness or ambiguity of their novels works as an effective way of exploring the connections and tensions between art and politics. The first half of this paper argues that Woolf`s subversive writing “inside/outside the boundary” -- A Room of One`s Own, and Jacob`s Room -- criticizes the male`s exclusive attitudes. The second half of this study suggests that a white woman narrator`s writing “between the boundaries” in Coetzee`s Foe is closely aligned to the “postcoloniality” and “feminism” of a colonial male writer. Thus, the conclusion is drawn that the “trans-/boundary” writing of Woolf and Coetzee develops into political, aesthetic, and ethical writing in terms of de-constructing hierarchy and leading to reflective thinking.