Jolly Squire character jug produced by Ricard Studio of England circa 1965. In the Middle Ages, a squire was the shield- or armor-bearer of a knight. Use of the term evolved over time. Initially, a squire served as a knight's apprentice. Later, a village leader or a lord of the manor might come to be known as a squire, and still later, the term was applied to members of the landed gentry, as in the case of this fine gentleman.