In this article I compare Michael Oakeshott's and Jürgen Habermas' respective accounts of morality, rationality and politics. I show that they both theorise the conditions of the modern political community as a ‘civil association’, and I argue that this comparison enables us to challenge predominant understandings of each thinker and to address criticisms levelled against them. I demonstrate that the contextualist and Hegelian aspects of Habermas' earlier work are carried over into his later work on discourse ethics and that he puts forward a more situated understanding of rationality and morality than is usually acknowledged. I also show that Oakeshott is not a straightforward conservative and in some respect he can be seen as a forerunner of deliberative politics. However, this comparison takes us beyond an exercise in interpretation, and I also draw attention to the practical possibilities residing in the work of Oakeshott and Habermas. Indeed, it is my contention that each of their approaches has much to offer in addressing the challenges of pluralism characteristic of contemporary multicultural societies and that their respective works can contribute to a contemporary theory of critical republicanism.