This chapter explores the relationship of Chaucer and his literary work to the wider chivalric culture in which he lived. It discusses the developments over the course of the fourteenth century to the status, significance and remit of the gatekeepers of chivalric knowledge, the officers of arms. Heraldry, the language of chivalry, was omnipresent in the late medieval world and encapsulated status, genealogy and affinity. During the fourteenth century it emerged from exclusively aristocratic usage to include widespread adoption by the gentry and the urban patriciate. Chaucer was himself armigerous and operated at the practical fringes of chivalric culture through work such as overseeing the erection of scaffolds for the Smithfield tournaments of 1390, providing witness testimony in the Court of Chivalry in 1386, and through his wider social life with prominent officers of arms such as his father-in-law, Guyenne King of Arms.