In this article, I claim that Wittgenstein was familiar with Hamann’s work, particularly with two of the latter’s original contributions: (a) the idea of transforming Luther’s concept of grammar into a critical philosophical and linguistic tool; and (b) Hamann’s use of a kenotic, impure style as a means to attain the humility his religious stance demands. I suggest that an understanding of Hamann’s style as a tool to achieve humility sheds light on Wittgenstein’s later refutation of the purity of the Tractarian style. As reflected in remarks published in collections such as Culture and Value and Public and Private Occasions, Wittgenstein – like Hamann – aspired to modesty not only in his private life, but also in his philosophical work, attributing it a religious significance. In this context, his later style of philosophizing, characterized by the use of everyday rather than metaphysical terms, the inclusion of impure concepts and humble examples, dialogue and fragmentariness, is a means to ‘dismantle one’s pride’, in the practice of philosophy conceived as ‘working on oneself’.