He was one of the Berkshire gentry while continuing as a clothier, becoming a 

Justice of the
Peace and a Member of Parliament, representing Great Bedwyn in 1545 and Cricklade in 1547. He
may possibly also have served in earlier Parliaments; records for these are incomplete. [13]
As one of the county gentry, John Winchcombe was asked to provide Newbury men to fight in Henry
VIII's armies, beginning when he was listed as one of those to be approached "…for aid against the
rebels in the north" (i.e. the Pilgrimage of Grace) in 1536.[14] He was listed to supply men for the army
in Flanders in 1543, with 10-foot soldiers specified; [15] and for the Boulogne campaign in 1544. [16] For
the latter, contemporary documents show him at the head of 150 named Newbury men, all furnished
with new coats. His will of 1557 includes references to 20 sets of armour and two demi-lances. [17]
He was among those present for the reception of Henry VIII's fourth wife Anne of Cleves,[18] and his
personal contacts included Sir Thomas Gresham[19] and the Protector Somerset.[20] He was granted a
coat of arms,[21] and had his portrait painted in 1550. [22]