The current study examines the historical and social elements of 14th century England, through Geoffrey Chaucer’s poem, Prologue to theCanterbury Tales. the study also unfolds the analogy of the current situation
of developing countries with Chaucer's era. The research is carried out, using the lens of New Historicism as a framework. New Historicism is a postmodern critical theory presented by Stephen Greenblatt (1943). The purposive sampling technique is used to proceed with the study because the research is descriptive in nature. Geoffrey Chaucer is considered as a father of the art of characterization. He placed his characters in the prologue from almost every walk of life, the characters reflect the historical and cultural background of 14th-century England. The history of Medieval England is traced down by analyzing the writings of Chaucer. Chaucer picked coomon characters from various fields to give an accurate picture of 14th-century England.