Shakespeare’s comedies Much Ado About Nothing and As You Like It interrogate Renaissance gender norms by subverting the institution of marriage, which represents the patriarchal order. Through Beatrice’s “phallic wit” and Rosalind’s cross-dressing as Ganymede, Shakespeare destabilizes the binary structure of gender, exposing it as a malleable social construct rather than an innate truth. By framing gender as performative and marriage as both a mechanism of control and its subversion, the plays reveal the paradox of marriage: it enforces gendered hierarchies while simultaneously enabling their undoing, questioning the legitimacy of binary gender roles and the societal hierarchies they uphold. Shakespeare’s characters breaking away from social norms is more than a reversal of male and female roles—it wholly questions the binary structure of gender as set by society. His works not only entertain but also provoke reflection on the instability of social constructs, resonating with modern discussions of gender and power. This article contributes to early modern gender studies by demonstrating how Shakespeare’s comedies highlight the instability of social constructs, using theatricality to expose the artificiality of power. Engaging with the proto-feminism debate, it moves beyond binary oppositions of subversion versus containment, proposing a hybrid model of Renaissance gender politics—one that acknowledges both the constraints of patriarchy and the spaces of resistance within it.