Oakeshott was the son of Frances Maude (Hellicar) and Joseph Francis Oakeshott, a civil servant and a member of the Fabian Society. George Bernard Shaw was a friend. Michael Oakeshott attended St George's School, Harpenden, from 1912 to 1920. He enjoyed his schooldays, and the Headmaster, Cecil Grant, later became a friend.
In 1920 Oakeshott became an undergaduate at Gonville and Caius College, Cambridge, where he read history. He obtained an MA and subsequently became a Fellow. While he was at Cambridge he admired the British idealist philosophers J. M. E. McTaggart and John Grote, and the medieval historian Zachary Nugent Brooke. The historian Herbert Butterfield was a contemporary and fellow member of the Junior Historians society.
Oakeshott was dismayed by the political extremism that occurred in Europe during the 1930s, and his surviving lectures from this period reveal a dislike of National Socialism and Marxism.
Although Oakeshott, in his essay "The Claim of Politics" (1939), defended the right of individuals not to become directly involved, in 1941 he joined the British Army. He reportedly wished to join the Special Operations Executive (SOE), but the military decided that his appearance was "too unmistakably English" for him to conduct covert operations on the Continent. He was on active service in Europe with the intelligence unit Phantom, which had connections with the Special Air Service (SAS), but he was never in the front line.
In 1945 Oakeshott was demobilized and returned to Cambridge. In 1947 he left Cambridge for Nuffield College, Oxford, but after only a year there he secured an appointment as Professor of Political Science at the London School of Economics (LSE), succeeding the leftist Harold Laski. He was deeply unsympathetic to the student activism at LSE during the late 1960s, on the grounds that it disrupted the work of the university. Oakeshott retired from the LSE in 1969.
In his retirement he retreated to live quietly in a country cottage in Langton Matravers in Dorset. He lived long enough to experience increasing recognition, although he has become much more widely written about since his death.
Oakeshott refused an offer of being made a Companion of Honour, for which he was proposed by Margaret Thatcher.
Oakeshott's early work, some of which has been published posthumously as What is History? And Other Essays (2004) and The Concept of a Philosophical Jurisprudence (2007), shows that he was more interested in the philosophical problems that derived from his historical studies than he was in the history, even though he was employed as a historian.
Oakeshott published his first book, Experience and its Modes, in 1933. He noted that the book owed much to Georg Wilhelm Friedrich Hegel and F. H. Bradley; commentators also noticed resemblances between this work and the ideas of thinkers such as R. G. Collingwood and Georg Simmel.
The book argued that our experience is usually modal, in the sense that we always have a governing perspective on the world, be it practical or theoretical. There are various theoretical approaches one may take to understanding the world: natural science and history for example are separate modes of experience. It was a mistake, he declared, to treat history as if it ought to be practised on the model of the natural sciences.
Philosophy, however, is not a modal interest. At this stage of his career, he saw philosophy as the world seen sub specie aeternitatis, literally, 'under the aspect of eternity', free from presuppositions, whereas science and history and the practical mode relied on certain assumptions. Later (there is some disagreement about exactly when), Oakeshott adopted a pluralistic view of the various modes of experience, with philosophy just one 'voice' amongst others, though it retained its self-scrutinizing character.
The dominating principles of scientific and historical thought were quantity (the world sub specie quantitatis) and being in the past (the world sub specie praeteritorum), respectively. Oakeshott distinguished the academic perspective on the past from the practical, in which the past is seen in terms of its relevance to our present and future. His insistence on the autonomy of history places him close to Collingwood, who also argued for the autonomy of historical knowledge.
The practical world view (the world sub specie voluntatis) presupposed the ideas of will and of value in terms of which practical action in the arenas of politics, economics, and ethics made sense. Because all action is conditioned by presuppositions, Oakeshott was inclined to see any attempt to change the world as reliant upon a scale of values, which themselves presuppose a context of experience. Even the conservative disposition to maintain the status quo relies upon managing inevitable change, he would later elaborate in his essay 'On Being Conservative'.
During this period Oakeshott published what became his best known work during his lifetime, the collection entitled Rationalism in Politics and Other Essays (1962). Some of the polemics against the direction post-World War II Britain was taking, in particular the acceptance of socialism, gained Oakeshott a reputation as a conservative, seeking to uphold the importance of tradition, and sceptical about rationalism and fixed ideologies. Bernard Crick described him as a 'lonely nihilist'.
Oakeshott's opposition to what he considered Utopian political projects is summed by his use of the analogy (possibly borrowed from the Marquess of Halifax, a 17th-century English author whom he admired) of a ship of state which has "neither starting-place nor appointed destination...[and where] the enterprise is to keep afloat on an even keel". He was a critic of the Cambridge historian E. H. Carr, historian of Soviet Russia, claiming that Carr had an uncritical attitude towards the Bolshevik regime, taking some of its propaganda at face value.
In his essay "On Being Conservative" (1956) Oakeshott explained what he regarded as the conservative disposition: "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, the sufficient to the superabundant, the convenient to the perfect, present laughter to utopian bliss."
Oakeshott's political philosophy, as advanced in On Human Conduct (1975), is free of any form of party politics. The book's first part ("On the Theoretical Understanding of Human Conduct") develops a theory of human action as the exercise of intelligent agency in activities such as wanting and choosing, the second ("On the Civil Condition") discusses the formal conditions of association appropriate to such intelligent agents, described as "civil" or legal association, and the third ("On the Character of a Modern European State") examines how far this understanding of human association has affected politics and political ideas in post-Renaissance European history.
Oakeshott suggests that there had been two major modes or understandings of human social organization. In the first, which he calls "enterprise association" (or universitas), the state is understood as imposing some universal purpose (profit, salvation, progress, racial domination) on its subjects. By contrast, "civil association" (or societas) is primarily a legal relationship in which laws impose obligatory conditions of action but do not require choosing one action rather than another.
The complex, often technical style of On Human Conduct found few readers, and its initial reception was mostly one of bafflement. Oakeshott, who rarely responded to critics, used an article in the journal Political Theory to reply sardonically to some of the contributions made at a symposium on the book.
In his posthumously-published The Politics of Faith and the Politics of Scepticism, Oakeshott describes enterprise and civil association in different terms. Here, an enterprise association is seen as based in a fundamental faith in human ability to ascertain and grasp some universal "good" (i.e. the Politics of Faith), and civil association is seen as based in a fundamental scepticism about human ability to either ascertain or achieve this good (i.e. the Politics of Scepticism). Oakeshott considers power (especially technological power) as a necessary prerequisite for the Politics of Faith, because a) it allows people to believe they can achieve something great (e.g. something universally good), and b) it allows them to implement the policies necessary to achieve their goal. The Politics of Scepticism, on the other hand, rests on the idea that government should concern itself with preventing bad things from happening rather than enabling ambiguously good events.
Oakeshott employs the analogy of the adverb to describe the kind of restraint law involves. To him, laws prescribe "adverbial conditions" - they condition our actions, but do not determine the substantive ends of our choices. For example, the law against murder is not a law against killing as such, but only a law against killing "murderously". Or, to choose a more trivial example, the law does not dictate that I have a car, but if I do, I must drive it on the same side of the road as everybody else. This contrasts with the rules of enterprise association in which those actions required by the governing are made compulsory for all.
The final work Oakeshott published in his own lifetime, On History (1983) returned to the idea that history is a distinct mode of experience, but built on the theory of action developed for On Human Conduct. Much of On History had in fact been written at the same time, in the early 1970s.
During the mid-1960s, Oakeshott declared an admiration for Wilhelm Dilthey, one of the pioneers of hermeneutics. On History can be interpreted as an essentially neo-Kantian enterprise of working out the conditions of the possibility of historical knowledge, work that Dilthey had begun.
The first three essays set out the distinction between the present of historical experience and the present of practical experience, as well as the concepts of historical situation, historical event, and what is meant by change in history. On History includes an essay on jurisprudence ('The Rule of Law') and a pessimistic re-telling in the modern setting of the story of 'The Tower of Babel', in which modern Western societies fall victim to their own materialism and greed.
Oakeshott's other works included a reader on The Social and Political Doctrines of Contemporary Europe consisting of selected texts illustrating the main doctrines of liberalism, national socialism, fascism, communism, and Roman Catholicism (1939). He was editor of an edition of Thomas Hobbes's Leviathan (1946), for which he provided an introduction recognized as a significant contribution to the literature by later scholars such as Quentin Skinner. Several of his essays on Hobbes were published during 1975 as Hobbes on Civil Association. He wrote, with his Cambridge colleague Guy Griffith, A Guide to the Classics, or How to Pick The Derby Winner (1936), a guide to the principles of successful betting on horse-racing; this was his only non-academic work. He was the author of well over 150 essays and reviews, most of which have yet to be republished.
Just before he died, Oakeshott approved two edited collections of his works, The Voice of Liberal Learning (1989), a collection of his essays on education, and a second, revised and expanded edition of Rationalism in Politics itself (1991). Posthumous collections of his writings include Morality and Politics in Modern Europe (1993), a lecture series he gave at Harvard in 1958, Religion, Politics, and the Moral Life (1993), essays mostly from his early and middle periods, The Politics of Faith and the Politics of Scepticism (1996), a manuscript from the 1950s contemporary with much of the material in Rationalism in Politics but written in a more considered tone.
The bulk of his papers are now in the Oakeshott archive at the London School of Economics. Further volumes of posthumous writings are in preparation, as is a biography, and during the first decade of the 21st century a series of monographs devoted to his work were published.