Daoism is China's earliest philosophical system. Discussions of philosophical and social issues in the Laozi, by the founder of Daoist thought, have had an enormous impact on Chinese intellectual history. The Laozi does not contain many arguments directly concerning art or the aesthetic. But another great representative of the Daoist school, Zhuangzi, made a major contribution to Chinese aesthetics. Arguments by Zhuangzi have been applied by his successors to the arts, to develop important aesthetic propositions. These ideas were particularly influential during the aesthetic developments of the Wei and Jin Dynasties (220-420). Individuals and artworks from this period developed new philosophies of art and a unique aesthetic consciousness. Chinese calligraphy is a unique art form, in which the creation of the written form expresses the aesthetic concept of harmony. Characters are created with form and line, and are consciously imbued with the spirit and meaning of natural affective forms. Calligraphy expresses the myriad forms and structures of nature, and also incorporates the natural beauty of affective forms into the shapes of written language. Wang Xizhi was an important Jin Dynasty calligrapher, often referred to as the "Sage of Calligraphy". His artistic creativity was intimately bound up with Daoist concepts, such as natural law, being and non-being, substantial and insubstantial, yin and yang, and the golden mean. This paper discusses the distinctive expression and aesthetics of Wang Xizhi's calligraphy.