“One is not born, but becomes a woman.” Simone de Beauvoir’s famous declaration of femininity as a socially constructed rather than innate quality captured the imagination of many Japanese women who came of age in the early postwar years, when Occupation-era reforms promising equality of educational opportunity seemed to offer liberation from this construct. Women of this generation flocked to courses in philosophy and literature, where they were inspired by philosophers like Beauvoir whose ethos of radical freedom suggested new possibilities for feminine self-actualization. Having successfully competed with men for these placements on what appeared to be a field of equality, many of these women were surprised to discover that their presence in the hallowed halls of academia was met with scorn by fellow students and professors, who presumed the very notion of an “intellectual woman” to be an oxymoron. How did these women navigate contradictory discourses of gender that extended such opportunities to them on one hand while discriminating against them on the other? How did philosophical tools aid them in establishing their place in the bundan, or literary world, even as philosophy itself was presumed to be a strictly masculine intellectual endeavor? This paper explores the thought and careers of cerebral women writers such as Kurahashi Yumiko, Saegusa Kazuko, and Takenishi Hiroko, who grappled with the possibilities of feminist philosophy at a time when the concept itself was illegible to most Japanese academics.