Widely considered a conservative British philosopher, this article presents Michael Oakeshott as, in fact, a critic of conservatism - in particular of the German conservative tradition, represented, among other thinkers, by Ferdinand Tönnies. This tradition was characterised by the rejection of modern individualistic society considered as an embodiment of alienating purpose-oriented rationalism. At a certain phase of his intellectual development Oakeshott himself came under the influence of this conservative critique, with ideas strikingly similar to those of Tönnies. Yet, unlike Tönnies, Oakeshott later rejected the premises of this tradition. Instead, he formulated the notion of rationalistic non-purposive association, which allowed him to become reconciled to modern liberal society.