This paper investigates how the age-old masculinity is subverted and interrogated by Angela Carter in her novel The Passion of New Eve. Carter rebels against patriarchy by transforming the sexual identity of the major protagonist (Evelyn), from male to female. Carter presents most of her female characters as strong and powerful where males are feeble and forced to sustain in the women’ autonomy. Gender is constructed not natural which is verified through Tristessa’s bogus presentation of femininity because, in fact, this character is a male. Depending on the theoretical acumens of, primarily, Foucault, Butler, Bakhtin and many other critics, the paper vindicates that gender is patriarchal product where the females are always given vulnerable positions. Teaching Evelyn a lesson means giving the novel on the hands of patriarchy by using the transgender narrative.