As seen in the previous chapter, one’s attire in the Middle Ages (and indeed in most ages) held symbolic and real value. What a person wore in medieval England was almost uniformly interpreted as an external representation of that individual’s social class. Chaucer’s portraits of the pilgrims in the General Prologue to the Canterbury Tales are perhaps the best-known examples of a poet describing the various modes of dress and costume that the pilgrims wear. Nevertheless, Chaucer is not without his own biases regarding his creation of the literary illustrations of the pilgrims. The portraits should not be read or interpreted as being universal descriptions; rather, these descriptions are Chaucer’s own metaphorical representations of the various classes and occupations in late fourteenth-century England. This complexity of the pilgrims’ attire (and how one could interpret one’s own outer and inner selves) is made all the more multifaceted when we examine Chaucer’s descriptions of the pilgrims within the context of the Ellesmere manuscript, Huntington Library MS EL 26 C9. The twenty-three equestrian portraits of the pilgrims, which are thought to be the work of three artists, add yet more layers of authorship, authority, and interpretation to the pilgrims’ textual and visual representations.