This study aims to derive the criteria of folding techniques and their characteristics through analysis of literature and previous studies. This will be realized by performing a case study on male fashion design and folding. It will propose diverse directions and data for male fashion design, by making men’s jackets using a folding technique. The concept and terms of folding were clarified through examination of existing literature and previous studies. Specifically, four pieces were created with motifs of the four seasons. Among the types of pleats expressed in the works, composition pleats include double ruffles, gathers, and draperies, while processed ones include box pleats, knife pleats, and accordion pleats. This study expresses continuity, fluidity, scalability, and ambiguity through the use of such pleats. The results of the production are as follows. First, in terms of the continuous use of regular and repetitive pleats, a possibility of rich pleats was confirmed because they varied depending on the gap between the pleat and target material. Second, in liquid but irregular pleats, diverse moods were created by the pleat movement. The overlapping of repeated pleats expresses diverse spaces and shapes in a 3D extended silhouette. Third, in pleat classification, ambiguity was confirmed with the use of continuous accordion pleats in the printed gradation fabric. It is anticipated that more diverse and creative designs could be created using more extended techniques in future studies.