Born in Leigh-on-Sea, Shires was an apprentice with local club Southend United, where he made one substitute appearance in the 1965–66 season.
[2][3][4] Shires was released by Southend in the summer of 1966 and taken on trial and subsequently signed by Essex rivals Colchester United.
[5] His first goals came in a 3–2 away win over Reading on 8 October 1966, the second of which was a last-minute match winner.
[2][6] Shires went on to play 23 times for Colchester, scoring one further goal[7] during a 5–3 home defeat to Torquay United on 4 November 1967.
[2][9] Shires was released from Colchester in the summer of 1968, subsequently joining Chelmsford City.