From a fairly poor background, one of Oakeshott's ancestors on his mother's side was the portrait painter Daniel Dodd.
His younger brother, Harold, was husband of Grace Oakeshott, an activist for women's rights;[1] his sister Violet married the economist and social reformer Gilbert Slater.
[2] After a grammar-school education, in the course of which he distinguished himself in French, he joined the civil service at the age of 16 as a "boy clerk", a new fast-track apprenticeship designed to prepare candidates for positions in the administrative class of the bureaucracy.
[4] In 1898, he married Frances Maude, daughter of Islington silk-merchant Thomas Hellicar; a son was the philosopher and political theorist Michael Oakeshott.
[5] Through the Hellicar wealth, the Oakeshotts were able to live comfortably- with "a substantial house (owned by Frances's brother), a cook, a gardener, and... Swedish lady chauffeur.