Educated at Wellington College Robin Oakley was assistant editor of the Daily Mail from 1981–1986. Between 1986 and 1992, he was a columnist and political editor for The Times. He then moved to the BBC, where he was chief political editor between 1992 and 2000. During this period he regularly presented political news items on BBC television news and the BBC Radio 4 programme The Week in Westminster. 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, which is his current position.
He was awarded an OBE in 2001 for his services to political journalism.
His 2001 book Inside Track is based on his experiences as a political journalist. Oakley's interests outside of politics include horseracing.