In Critique of Judgment, Kant introduces a foundational theme in modern aesthetics by identifying the judgment of taste as a particular mode of attention. In distinction to the mode of attention in mundane experience that works by determining how an intuition can be subsumed under a concept, aesthetic attention celebrates the pleasure associated with the “unison in the play of the powers of the mind” confronted with “the manifold in a thing.” Aesthetic attention, in other words, is an aesthetic subject’s attention to itself and to the pleasures derived from flexing the power of imagination. In this respect, Kant’s aesthetics reaffirms its cartesian core, the primordial positing of the thinking and reflective I as the necessary preposition for experience. This strict distribution of attention toward the secure epistemological architecture of object and subject seems to vacillate, however, in Kant’s brief discussion of artworks as purveyors of “aesthetic ideas.” This article discusses the de-limitation of attention instigated by the aesthetic idea. The aesthetic idea is associated with the artwork as an object, but it immediately transgresses the limits of the object through an array of analogical instantiations of “spirit.” On the other hand, aesthetic ideas are subjectively appreciated, but this appreciation similarly transgresses subjective cognition in an inexhaustible ramification of associative thinking. Developing these characteristics of the “aesthetic idea,” the article proposes to excavate from Critique of Judgment a mode of aesthetic sensibility that eventually challenges the Cartesian architecture of subject and object and thus reposits aesthetics in a field of relational interdependency.