This paper analyzes fashion in medieval literature as a means of self-representation that reflects the wearer’s honesty or dishonesty concerning their struggle with societal status. In the “General Prologue,” Chaucer depicts a wealth of characters who capture this honesty and dishonesty of clothing in the fourteenth century, mirroring dress and self-representation in modern society. How one chooses to present themselves to the world is not only a reflection of themselves. It is also a reflection of how idealized expectations and clothing’s illusion affect one’s comfort disseminating a true identity. Pieces analyzed include the Knight’s armor, the Prioress’s gold broach, the Wife of Bath’s red hose and wimple, and other noteworthy costume components demonstrating this Chaucerian concept. However, the idea is paralleled in modern times as well. As brands continue to grow and the apparel industry moves toward fast-fashion models, the lines become blurred, and one can use fashion to either reveal or hide who they really are. In the twenty-first century, clothing can deceive, as copy-cat fabrics and the façade social media and fast fashion facilitate run rampant. In this paper, I assert that dishonest clothing is dress that is selected with the intent or purpose of showing society a form of the individual that is not entirely authentic. Through idiosyncratic apparel descriptions and the use of fashion as a metaphorical device, Chaucer’s “General Prologue” serves to highlight this façade—witnessed in both the fourteenth century and today. This paper functions to address the concept of dishonest and honest clothing as it pertains to medieval literature and the implications that arise when viewing the textual evidence under a modern lens.