Geoffrey Chaucer (c.1342–1400), a public servant and a poet, was the most important writer of Middle English. As the son of a London wine merchant, he was a member of the growing middle class in England. Much of his life was spent in the company of royalty, however. By 1357, he had entered the service of Elizabeth, countess of Ulster, and had met John of Gaunt, who would become one of his chief patrons. Chaucer's favor with the aristocracy continued to grow. King Edward III contributed to his ransom after Chaucer was captured during an invasion of France in 1359. In 1367, he was granted a life pension by the king and subsequently returned to France and Italy on several diplomatic missions. For the rest of his life, he continued his civil work as a Controller of Customs, a justice of the peace, a member of Parliament, and a Clerk of the King's Works. In his old age, he was generously provided for by both Richard III and Henry IV. Despite all of his work as a public servant, Chaucer found time to write poetry.

Chaucer was widely read and educated on a variety of subjects. His first literary influences were the French allegorical poets, who were popular with the English aristocracy of the time. One of his first known works is "The Romaunt of the Rose," a translation of a French poem. The Book of the Duchess, one of his earliest original works, was written as an elegy for John of Gaunt's first wife. A diplomatic journey to Italy in 1372 put Chaucer in direct contact with the Italian Renaissance, giving him new ideas for subjects and forms for his own writing. Boccaccio served as a source for both Troilus and Criseide and for "The Knight's Tale" in The Canterbury Tales, considered the major literary achievement in Middle English. Chaucer wrote both poetry and prose on a wide range of subjects, drawing on his own broad reading and on his varied personal experience.