The paper aims to explore the different environmental conditions that favored the development of wool and silk trade in England and Byzantium, respectively, and to study the economic, political, religious and cultural dimensions of it. Wool was the most important source of wealth in medieval England and the principal means of financing the Hundred Years’ War between England and France. Wool manufacturing had a great impact on the society and provided an important foundation for medieval urbanization. Byzantium, on the other hand, established a monopolistic imperial silk weaving industry from the fourth century onwards. The Byzantines demonstrated their technological superiority in silk art crafts and impressed the West that assimilated it and tried to imitate it.