Stanley was educated at the Judd School, a grammar school in Tonbridge, Kent. He then attended Trinity College, Cambridge, where he studied modern history. He graduated from the University of Cambridge with a Bachelor of Arts (Bachelor) degree (later promoted to Master of Arts (Cantab) as per tradition), a Master of Philosophy (Master of Philosophy) degree and a Doctor of Philosophy (Doctor of Philosophy) degree.
His doctoral thesis was on Edward M. Kennedy"s role in the United States Democratic Party in the 1980s, which was published in 2010 as his first solo book, Kennedy versus Carter: The 1980 Battle for the Democratic Party"s Soul. At Cambridge he was active in student journalism.
Stanley also unsuccessfully ran for a sabbatical post on Cambridge University Students" Union, standing in 2007 for Welfare Officer.
His manifesto consisted of a handwritten note simply reading "This is hand written because I was too drunk to write a manifesto. There is no better testament to my character".
He is the recipient of a Leverhulme Trust Grant. In November 2011, he organised a conference called History: What is it good for?, which generated some controversy after one of the speakers, David Starkey, said that the national curriculum in British schools overlooks British culture.
Since 2011, Stanley has been a regular blogger and occasional columnist for the Daily Telegraph, reporting on American politics and culture, particularly the 2012 Republican primaries.
He contributes to History Today, and has written pieces for Cable News Network, The Guardian and The Spectator. He wrote and presented a documentary for the British Broadcasting Corporation entitled Family Guys? What Sitcoms Say About America Now, which was broadcast in October 2012. He is also an occasional pundit on British Broadcasting Corporation News, Consumer News and Business Channel, Sky News and Channel 4 News.
Stanley joined the British Labour Party at the age of 15.
He was Chair of Cambridge University Labour Club in 2003-2004, and stood as the Labour candidate for his home constituency of Sevenoaks at the 2005 general election, where he came third. He has since distanced himself from the Labour Party, and has been arguing in support of the United States Republican Party.
He is widely seen as being a supporter of David Cameron"s post-2005 Conservative party. In October 2012, Stanley stated he was "raised a good Baptist boy".
Later, he considered himself to be an Anglican, beginning around "one glorious summer" in 2002, and was baptised as an Anglican in Little Saint Mary"s, Cambridge in New Year 2003.
Stanley held lectureships at the University of Sussex in 2008-2009 and Royal Holloway, University of London in 2009-2011, and from 2011 to 2012 he is an associate member of the Rothermere American Institute at the University of Oxford.
