In the year 1642, when the differences between Charles I and Parliament made armed conflict inevitable, there was appointed as quartermaster to the troop of horse commanded by Lord Brooke in the Parliamentary army, one John Okey, the proprietor of a ship chandler’s business near the Tower of London. His father had property in London in the parish of St. Giles in the Fields and the family arms were : or, on a fess sable, between three mascles gules, as many plates azure. The young John and his brother Thomas had both been married at the church of St. Giles in the Fields—John to Susanna Pearson on 21 January, 1630, and Thomas to Ann Carter on 16 May, 1629.

The little that is known of John Okey’s life before 1642 is gathered chiefly from the pens of those hostile to the cause which he was to espouse so warmly. Thus Anthony a Wood refers to him in disparaging words ‘His parentage was as mean as his calling, having been originally as ‘tis supposed a drayman, afterwards a stoaker in a brew house at Islington near London, and then a poor chandler near Lyonkey in Thame Street in London.’ Another contemporary wrote : ‘First he belonged to a Brew-House as a drayman, after that a poor Chandler near Lyon’s Key,’ while a third contented himself with the observation : ‘The low extraction of Okey is buried in obscurity. Being a Tallow-Chandler in London.’ The Republican Ludlow, however, refers to him as a citizen of London and his appointment as quartermaster at the outset of war, seems to confirm that he had some standing in the City, possibly as a member of the trained bands. His rapid promotions and his subsequent career were proof of his innate ability.

King Charles set up his standard at Nottingham in August 1642 and later moved to Shrewsbury. The Parliamentary army under the Earl of Essex, which was superior in numbers, left London on 9 September and marching by way of Northampton, Rugby, Coventry and Warwick reached, and on 24th occupied, Worcester, which the royalist commanders, Sir John Byron and Prince Rupert had evacuated in spite of their recent victory at Powick Bridge over a body of Parliamentary horse.