Born the son of Group Captain (later Air Chief Marshal Sir) Walter Cheshire, and educated at Ipswich School and Worksop College, Cheshire joined the Royal Air Force as an officer cadet at the RAF College Cranwell in 1961.

[6] In the late 1970s, Cheshire served as Commander of the Special Forces Flight, and then joined the Air Plans Directorate of the Ministry of Defence.

[10] He was promoted to air vice marshal on 1 January 1992,[11] and appointed Assistant Chief of Staff Policy and Requirements at the Supreme Headquarters Allied Powers Europe.

[1] As an acting air marshal, he was appointed a Companion of the Order of the Bath in the 1994 New Year Honours.

He was appointed chairman of the Royal Air Force Charitable Trust in July 2008.