This contribution aims to relate an important topic of the Hegelian philosophy, that of second nature, to the gender question developed by Simone de Beauvoir. The core of the emancipation process described in The Second Sex lies in Beauvoir’s revolutionary idea of the artificial character of gender: the latter belongs to the culturally constructed sphere of social norms and not to mere fixed nature. In this assumption the French philosopher seems to recover the Hegelian theory of second nature: Hegel believes that through an individual and social Bildungsprozess, subjects liberate themselves from the immediate level of natural necessity and reach the free horizon of spiritual existence, in which they become self-conscious actors. Beauvoir accepts in her own existentialist view this extra-natural becoming and realizes that also gender participates in it: women are not by nature ‘immanent’ creatures that lack ‘transcendence’. Hegel, however, does not recognize the second nature of gender and falls into that same essentialism, denounced by Beauvoir, which relegates the woman to the biological plane, thus excluding her from the dialectic of second nature and self-consciousness. For this reason, Hegel’s understanding of freedom through second nature will initially be introduced, and then, employing this concept against Hegel himself, the path of emancipation from gender essentialism in Beauvoir’s account of biology and culture will be addressed. In the second part of the paper it will be shown how gender, in acting as a second nature, replays the same ambiguity of Hegel’s theory: are second nature and gender something that we individuals freely shape or are we victims of an externally imposed necessity just like in first nature? A dialectical solution will be presented in both thinkers, whose work aims to conciliate spirit and nature beyond any Cartesian dualism.