This lecture will consider the complex intersections of esotericism, rationality, and gender, using as its starting point the gendered dichotomy of reason and unreason, central to the formation of modernity. Enlightenment philosophy upheld a masculinized ideal of disembodied, rational, and detached study and domination of a shadowy, unruly, and feminized natural world. This image hinges on a series of related gendered binaries: active-passive; mind-body; culture-nature; and light-darkness, with unreason ascribed to women and femininity. As Hanegraaff (e.g, 2012) has demonstrated, the binary of rationality and irrationality fundamentally shaped the emergence of the category of esotericism, which Enlightenment thinkers polemically ascribed to the realm of irrationality. The relationship between esotericism and rationality appears thornier, however, when viewed from the perspective of gender. In this lecture, I will discuss three illustrative examples of how esotericism has upheld, subverted, or destabilized the gendered dichotomy of reason and unreason. Firstly, I will consider women’s masonic activity around the turn of the century 1800, indicating how the rituals and symbolism of women’s lodges of Adoption indicated a positive valuation of women as seekers of knowledge and illumination and offered (elite) women a venue for challenging early-modern notions of female spiritual and intellectual inferiority. Secondly, I will consider the complex gender politics of Anglophone occultism around the year 1900. Fin-de-siècle occultism, formulated by its proponents as a scientific quest for spiritual knowledge, offered women of the growing middle-classes the opportunity to hone masculinized characteristics of reason and willpower. At the same time, occultist polemics against (female-dominated) Spiritualism (seen as passive and irrational) highlight how esoteric movements have frequently upheld gendered scripts. Thirdly, I will discuss the British occultist Kenneth Grant and his Typhonian Trilogies (published 1972–2002), indicating Grant’s vision of the transcendence of rational subjectivity as a desirable and feminized state. Through these examples, I will highlight how a consideration of gender offers new insights into the different ways esotericism has related to hegemonic systems of knowledge, as well as how the history of esotericism sheds novel light on how notions of reason have been shaped in the intersection with gender.