Alan Watts has been accused of never seriously practicing any of the spiritual disciplines that were central to the Eastern philosophies that he popularized in the West. This article puts forward a view of Alan Watts as practicing his general philosophical outlook through the "aesthetics" of his life—his possessions, friends, habits, and general lifestyle. Particularly in the second half of this essay, I explain that Watts built his life around people, places, and things that could not neatly fit into those three categories. For instance, he valued objects that had some humanity to them, while at the same time were deeply rooted in nature. This general example and many others that follow support the argument that the aesthetics of Watts’ lifestyle enacted the mystical blurring of lines between individuals and between individuals and their environments. In preparation for that point, this article offers a discussion of the complexities that important criticisms of Watts bring out, as well as the responses to those criticisms that are built into Watts’ work. Put together, the two strokes of this article offer a qualified defense of Watts as an important and interesting philosopher worthy of more credit than simply introducing many beatniks, counterculturalists, and new-agers to Zen, Daoism, and Hinduism.