In 1639, a law prohibiting women any head covering; veil, mantilla, manto for example, is promulgated for the fifth time in the Iberian Peninsula under the penalty of losing the garment, and subsequently incurring more severe punishments. Regardless of these edicts this social practice continued. My dissertation investigates the cultural representation of these covered women (tapadas) in Spain and the New World in a vast array of early modern literary, historical and legal documents (plays, prose, and regal laws, etc.). Overall, critics associate the use of the veil in the Spanish territories with religious tendencies and overlook the social component of women using the veil to simply explain it as a mere fashion practice. In my dissertation, I argue that it is more than just a garment; the veil was used by women to make political statements, thereby challenging the restrictive gender and identity boundaries of their epoch. A critical analysis of early modern historical and legal peninsular texts and close-readings of Golden Age literary works, together with colonial cultural productions, allow me to identify patterns in how the tapadas were represented both artistically and culturally. Accordingly, my project attempts to reassess the significance of the tapadas in Hispanic culture for 350 years and demonstrate how their resilience to stop using the veil publicly is symptomatic of the absolutist monarchy inefficiencies in imposing social control. I move away from the tendency to investigate works including tapadas exclusively, and I conclude by reconstructing more accurately their cultural impact on the social dynamics in Spain as well as the New World.