This article analyses the functions of monastic clothing in the first two generations of the Discalced Carmelite order, the reform of which was led in Spain by Teresa de Ávila from the 1560s to the 1580s. The source material used by the author is a re-reading of the most widely circulated spiritual treatises and hagiographical texts by the Discalced Carmelites, especially nuns, both in manuscripts and printed books, most of which were written in the beginnings of the seventeenth century. The purpose of this article is to overcome and complicate the assumption that monastic clothing is a mirror of religious virtues. This hagiographical commonplace is still widely shared by the historiography of monasticism. I advocate that far from being reducible to an unequivocal and impersonal speech as a virtuous language, the habit is a tool to get round the monastic rule. This paper focuses on the plasticity of the habit in this matter and argues that the ceremony of taking the veil is not a common rite of passage, but the opening of a confusing period during which each nun is asked to be on a par with the prescriptive dimension of the habit to which she is bound. It enhances the communitarian control of the habit and displays the differential uses of monastic clothing inside the monastic community. The habit is a means to distinguish any nun from among the others and to build and emphasize her reputation of sanctity inside the community, through a delicate play on the condition, cleanliness, and conformity of their own clothing. This social dynamic is crucial in times of monastic reform, when the habit is a way to enhance the specificities and defend the honor of a new religious order in its confrontation with worldly clothing and the habits of rival religious orders.