The Kiryū silk weaving district, located 200 kilometres north of Tokyo, has been one of the most advanced silk weaving districts since the Tokugawa period (1603–1868). In the 1870s, it was a pioneer in the export of silk products from Japan and the leading producer of traditional Japanese kimono and obi (sash belts) for domestic markets. This study finds that the developmental process of the Kiryū district from 1895 to 1930 can be divided into at least two phases, that is, one of gradual growth based on an inter‐firm division of labour using hand looms and one of dynamic development based on the factory system using power looms. Weaving manufacturers‐cum‐contractors pioneered gradual growth by sub‐contracting with rural village out‐weavers and with a number of specialized, supporting firms in Kiryū town, and grew faster than factory production systems. New joint‐stock firms played the role of genuine entrepreneurs by introducing power looms, thereby realizing significant economies of scale. During this new phase, the weaving manufacturers‐cum‐contractors survived and also introduced new production systems.