This article brings together two works by the fourteenth-century Italian author Giovanni Boccaccio: his public lectures, Expositions on Dante's Divine Comedy, and the Latin collection of biographies On Famous Women. Placing these texts in conversation with one another, this article analyzes the five women from antiquity—Lucretia, Julia, Lavinia, Penthesilea, and Camila—who appear in Dante's Inferno and both Boccaccian texts. The first half of the article evaluates Boccaccio's claim in the Expositions that the women in Inferno 4 shall be seated alongside philosophers in the afterlife. Through these women, Boccaccio connects the domestic sphere with philosophical knowledge, thereby undermining the idea that philosophy is only for erudite men in schools, and disrupting distinctions between practical and theoretical philosophy. The second half turns to Boccaccio's portrayals of the same female figures in On Famous Women. Examining how their representations in the Latin compendium compare—and, at times, conflict—with Boccaccio's writing in the Expositions, the article considers how Boccaccio problematizes what constitutes virtuous behavior and philosophical knowledge for women. It concludes that Boccaccio affirms that philosophy is available in the hearts and minds of men and women alike, and that praiseworthy women exist both within the domestic space and beyond it.