In this article I focus on the concept of habit in Kant’s philosophy. First of all, I concentrate on the criticisms he delineates against Gewohnheit in his epistemological and moral philosophy. In particular, habit is seen as absence of moral freedom. This conclusion is pretty different from Kant’s position expressed in his Anthropology From the Pragmatic Point of View and in the last part of the Conflict of the Faculties. After a deep insight on the different terms referred to the conceptual field of habit, I focus on the relation between Gewohnheit and desire: in fact, Kant recognized that habit is not the mere repetition of an act, but more precisely it is the desire of repetition. That is why it is not strictly bonded to the deterministic world and it does not refer to machines: only the living beings may have habits. This way, it is possible to understand its role within the theme of health: in the reflections on dietetics, habit is particularly useful. The last part of the article is devoted to the new perspective on Kantian political philosophy opened by this positive view on this concept.