Throughout his life Ortega y Gasset turned his attention to the definition and critical analysis of art and aesthetics, converting this theorization into a vital constituent of his philosophical system. In his own peculiar style, the Spanish thinker tried to understand the political, historical, and social disruptions of his time and their reflection in culture, aesthetics, and art in the early twentieth century. This chapter stresses the place of aesthetics in Ortega’s philosophical system and the role of metaphor as a source of existence and knowledge. We will focus on Ortega’s philosophical evolution and mainly on his theorization of art according to the two aesthetics or paradigms that had been prefigured from his first article “Adam in Paradise” (1910) to “Velázquez” (1959), stressing The Dehumanization of Art (1925) as a turning point in Ortega’s perspective toward the nature and purpose of art. In this masterpiece, Ortega recognized in avant-garde movements a new sensibility, concluding that what was lost in transcendence was gained in innovation. Albeit this new art form has no defined rules, it should be respected and supported, since it represents the artist’s subjectivity and perspectivism. Ortega’s sharp analysis raises new readings and interpretations that we aim to reevaluate in favor of a more syncretic reassessment.