The most stylish conservative philosopher of the 20th century — an LSE professor whose prose, dry and carefully paced, was itself an argument for the disposition he defended. Oakeshott's Conservatism is not a programme or a set of policies but a sensibility: "to be conservative is to prefer the familiar to the unknown, to prefer the tried to the untried, fact to mystery, the actual to the possible, the limited to the unbounded, the near to the distant…"
His target was "rationalism in politics" — the characteristic 20th-century conceit that political life can be rebuilt from abstract principles by experts armed with the right theory. Rationalism in Politics (1962) skewers this style wherever he found it: Marxist, technocratic, fascist, democratic-reformist. Real political knowledge, he argued, is practical knowledge — the tacit, accumulated know-how of an ongoing tradition — and cannot be reduced to rules in a book. Reduce it, and you get the book without the knowledge.
His most systematic work, On Human Conduct (1975), distinguishes two modes of association: civil (a society of people related by shared non-instrumental rules — like the rule of law) and enterprise (a society organized around a shared purpose, like a firm or army). The modern state, he thought, was increasingly and dangerously conceived as an enterprise association — a machine for delivering substantive goods — when it should be a civil association instead. This gives him an unexpected kinship with Friedrich A. Hayek, though his concerns are more philosophical than economic.