Following the development of the Industrial Revolution 4.0, many new types of systems are being designed, introduced, or attempted, even in almost every traditional industry. The clothing industry is no exception. The use of continuously developing production equipment and Information and Communication Technology (ICT) has a single objective, providing a customized service to all customers. Thus, in this study, the primary research task was to identify ill-balanced aspects or disadvantages of the services previously analyzed to construct a more complete online customized service. This was accomplished by analyzing an automated Computer-Aided Design (CAD) output file containing customer requirements regarding individual clothing items. The secondary research task was to plan and design a clothing manufacturing process to which a one-person one-item mass production system has been applied to achieve a customized service. As a result, for the primary research task, the customers’ requirements for each dress were reflected in attributes, such as color, pattern, or size, and it was possible to obtain an automated CAD output file for each element. Such CAD output files can be used in the production process directly. To find the possibility of upgrading the existing dressmaking process and implement the one-person one-item system, the entire manufacturing process was simulated for the test.