Chaucer's poems reveal much about the English medieval period.

First, the hegemony of Christianity in Europe grounds many of the assumptions in his texts. Belief in an afterlife of punishment or reward is implied not only in how characters are judged but in how they approach choices in this world.

The Middle Ages fostered a rich philosophical tradition, synthesizing the ancients with Christian writers such as Boethius, Augustine, and Aquinas. Chaucer's own poetry is especially steeped in Boethius, whose Consolation Chaucer translated into English. The notion of human temporal understanding versus divine atemporal understanding is prevalent in "The Knight's Tale" especially—where the problem of evil is everywhere confronted.

Especially in The Canterbury Tales, the notion of the feudal estates is important. The wide diversity of human types as well as the restlessness in society for upward movement creates tension that feudal societies sought to suppress. The pilgrims in this work mostly seek to evade the ideals of the feudal society and escape the confines of the estate into which they are placed. The poem works by creating ironic portraits of these failings.

Another quality one finds in Medieval literature is a strong desire to catalog and synthesize human knowledge. Chaucer's own work seems a catalog of the wide variety of genres written during the period. From lofty poems like Troilus and Creseyda, to The Canterbury Tales dynamic society, to Legend of Good Women's hagiography, Chaucer's texts embody the curiosity, sophistication, and delight in language that mark this era.