He started his career on the Liverpool Daily Post where he became Political Editor. He was then the Crossbencher columnist and assistant editor on the The Sunday Express and was assistant editor of the Daily Mail from 1981 to 1986. Between 1986 and 1992, he was a columnist and political editor for The Times. He then moved to the BBC, where he was Political Editor between 1992 and 2000. During this period he regularly presented political news items on BBC television news. His predecessor as BBC Political Editor was John Cole, and he was succeeded in 2000 by Andrew Marr. After leaving the BBC, Oakley became CNN's European Political Editor. He has since 1994 written the Turf column in The Spectator and was for several years the racing correspondent of the Financial Times.