Zhang Kejiu occupies an important position in the history of sanqu (colloquial song). Not only does the sheer volume of his sanqu songs account for one-fifth of the extant sanqu songs, but his significance also lies in the unique style of his songs. In particular, his sanqu songs hybridize traditional literary elements with the up-and-coming form of sanqu. This article examines how Zhang embodied the aesthetics of classical poetry in the format of sanqu through a detailed examination of meter, parallel lines, and rhyme. Also, to demonstrate that the synthetic style of Zhang's sanqu songs was not merely the result of combining literary and colloquial styles, this article aims to reconstruct Zhang's idea about poetic functions underlying his literary syncretism by exploring his literary activities in the cultural context at his time.