The Korean economy has transformed from the domestic home-based to the global mass production-based one since the Korean–Japan Treaty of 1876. New technologies such as the sewing machine and mass production systems were introduced to Korea simultaneously, and the result was the two new clothing retail operation types: custom-made and ready-made clothing stores. After reviewing over 340 daily newspaper articles and advertisements published from 1896 to 1938, the findings show the key characteristics of two Western-style clothing store types, the key marketing strategies that these two store types used, and the survival strategies that custom-made stores employed to compete against ready-made stores. Within the context of the Korean clothing industry today, the results of this study present interesting insights into how the Korean clothing industry was born and grew during the early 20th century when the country was emerging from a home-based handmade economy to a factory-based machine-made one.