The primary goal of this study is to reveal the strategies Kant occupied to render his concepts of the beautiful and the sublime in The Critique of Judgment. By exemplifying the similarities and differences between Kant's and Burke's analyses of the aesthetics, this paper proposes to illustrate the complexes and paradoxes in Kant's reflective judgment. When applying Kant's idea of pure aesthetic judgment to either literary texts or objects in reality, we can hardly neglect several philosophical antinomies in his ideas of free and dependent beauties. This study aims to question the existence of aesthetic purity as well as reclaim the function and meaning of the object as Kant focused merely on the inner feeling of the subject. His judgment of the sublime, on the other hand, presents a more consistent picture that reveals not merely his “sense of imaginative inadequacy” but also his optimistic belief in human reason and the supersensible power inside human mind.