This paper traces the development of Karl Philipp Moritz’s writings on aesthetics that were produced in the aftermath of the essay “Über den Begriff des in sich selbst Vollendeten” and that led up to the influential booklet Über die bildende Nachahmung des Schönen. The writings from this short period, stretching from 1786 through 1788, are epitomized by an increasing awareness of the deficiencies associated with man-made products, including works of art. Art is a formative imitation or imprint of nature’s eternal perfection but is in itself imperfect and transient. However, this lack of perfection is the very impetus behind all man’s ethical endeavors, that is, the struggle for nobility and love. By construing the work of art as fundamentally flawed and ephemeral, Moritz’s aesthetics problematizes the idea of perfection as well as the notion of aesthetic autonomy.