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Sir John Penruddock (c. 1591-1648) of Compton Chamberlayne, Wiltshire, came from a well established landed family in Wiltshire. He matriculated at Queen's College, Oxford on 1 July 1608 aged seventeen and was admitted at Gray's Inn on 18 March 1608/9. The present portrait, dated 1616 when he was twenty-five, shows the sitter in elaborate and costly dress, presumably for court, the floral motif embroidery evoking the notion of courtly love and chivalry.

Sir John is recorded as Sheriff of Wiltshire in 1635, and was appointed a Commissioner of Array by King Charles I to muster a Royalist Army in Wiltshire for the Civil War. He married Joan Meade and had four sons, receiving the D.C.L. from Oxford in 1643, the year in which he was knighted. He was a recusant and is now best known as the father of Colonal John Penruddock (c. 1620-1655), who led a rising against Oliver Cromwell and was executed at Exeter in 1655.

Sir John's will, dated 1 January 1647/8, was proved in the Prerogative Court of Canterbury on 10 June 1648. In it he describes his son John as his son and heir, so his elder son George Penruddock must have predeceased him. He also had younger sons Thomas and Edward. His widow died shortly after, and her will was proved on the same day as that of her husband.