This dissertation is a critical examination into various widely held beliefs about the nature of art by studying them through the lens of the art of classical dressage. Classical dressage is an illuminating case study for the philosophy of art because it has features which are remarkably distinctive compared to some more conventional arts. In this dissertation, I challenge widespread notions about these problems such as: the belief that exemplification of creativity is a necessary condition of 'art'; the belief that the moral implications of a work of art are irrelevant to our aesthetic judgment of the work; the argument that awareness of an object's function should bear no relation to our aesthetic assessment of it; the assertion that there is a fundamental incompatibility between sport and art that prevents sport from ever attaining the status of art; and the belief that the distinction between art and craft is based on creativity found in the art-making process that is lacking in the making of craft.