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Using iconographic sources drawn from a 13th century moral treatise, this article examines representations of measurement instruments and the gestures of those who measured or weighed. Around 1270, The Italian Dominican Jacobus de Cessolis wrote the Liber de ludo scacchorum, translated into English under the title The Moralized Game of Chess, which considers the chess game as an ideal city, with the pieces personifying the various states of society. In addition to their symbolic position on the chessboard, the author endows each pawn with a material image by listing the attributes which characterize its activity. For example, the merchant and the guardian of the cities are most often represented alongside measuring instruments, scales, weights or rules. Among the two hundred preserved manuscripts of this work, there are many illuminated versions, produced from 1318 and throughout the 15th century in France, Germany and Italy, that enable us to understand and compare the materiality and variety of medieval measuring instruments.