As a key critical term in the Augustan Age of English literature, “wit” has been abused and has become problematic. It denotes a faculty or a quality. It has many attributes: propriety, adornment, quickness, variety, synthesis, pleasure, resemblance, congruity, surprise, truth, creativity, etc. But proper adornment seems to be the most essential idea for the Augustans. The word engenders the problem of “true wit vs. false wit.” It is connected to the differentiation of wit from judgment. It is said to have “the old sense” and the new “dangerous sense.” It is divided into “wit writing” and “wit written.” It is compared to “a perfect conception with an easy delivery.” It is in fact considered in the light of criticism, poetry, and morality altogether, and found in a wide variety of manifestations. By the time of neoclassicism, it had become a signal word for extending arguments between rhetoricians and critics such as concerning simplicity vs. ornamentation, word vs. thought, reason vs. imagination, and delight vs. instruction, and it had been variously identified with intellect, understanding, judgment, imagination, etc. Our conclusion is: the Augustan “wit” can be dichotomized into “inward wit” and “outward wit,” can be a truth-finding “pre-composition power” and an expression-finding “composition power,” and can be analytical (critical) and synthetic (creative) at once. Under this condition, wit cannot be called true or false merely due to its being exercised on ideas (content) or on words (expression), althought we must admit that after the Ramist separation of rhetoric from dialectic, the Augustans had leaned towards the rhetorical side, thus valuing art over nature and regarding proper adornment or linguistic expression (the dress), rather than insightful truth (the body), as their primary concern. This Augustan “wit” naturally would be replaced by the Romantic “imagination,” which by nature and by definition in the course of historical change was a swing back to the dialectical side of truth.