Literary criticism is a kind of commentary genre, with a certain color of argumentation. Toulmin’s model, as an important method of non-formal logic, has played an important role in the analysis of argumentative discourse (Yang, 2004). Therefore, it also provides a new perspective for the study of literary criticism. This paper, on the basis of consummating Toulmin’s model, analyzes different specific arguments of The Well of Loneliness, this controversial literary work whether can become a literary classic and widely recognized in different times, combined with literary criticism, and tries to characterize the internal structure of the argumentation, analysis of the dynamic process of argumentation and improvement of the pragmatic strategies of argumentation in a finer way. Thereby, it is more rational to verdict and to verify the rationality and effectiveness of the argumentation. Then suggestions of the construction and perfection of literary criticism can be provided.