Tirso de Molina’s Don Gil de las calzas verdes is considered the quintessencial comedia de capa y espada play of the seventeenth century. It has achieved international acclaim and remains highly popular among theater audiences. At the core of its appeal is the unprecedented performance of the cross-dressed swash-buckling female lead whose intricate machinations maneuver her unsuspecting victims. Many critics have contributed valuable explorations of performance, gender and power to this subject. Despite these efforts, Don Gil’s ingenious dramatization of illusion has eclipsed significant inscriptions on the disillusionment of gender and class. This paper undertakes a historical and analytical study of the transvestite theme at a critical time of shifting identity formation. In the play’s heightened gender performance the concept of identity as moldable and variable emerges as a reflection of the new early modern awareness of the self. While the female cross-dresser provokes gratuitous titillation, lesbian nuances, and gender strife, a close-reading of gender fluidity will reveal other provocative cultural contingencies. A reevaluation of Tirso de Molina’s use of transvestism in Don Gil de las calzas verdes, uncovers poignant discourses that offer compelling insights into an evolving feminized Spanish society.This article does not follow the overall copyright policy of LL . © Jelena Sánchez 2006. All Rights Reserved.