The study aimed to investigate the wearing & purchase practices with shirts and analyze the group differences on the shirt size, BMI & perceived body type. Total usable questionnaires were obtained from 350 male office workers aged from 20 to 49 in Seoul. Results were gained from the statistical analysis such as factor analysis, ANOVA, t-test using SPSS 21.0. The results were as follows. First, male office workers had difficulty in choosing the right size among the different sizes of ready-made shirts and had trouble in vexatious order & high price for custom-made shirts, however, they had an emphasis on design and size for the 2 kinds of shirts in common. Second, the groups by shirt size, BMI, perceived body type showed significant differences in shirt fitness and shirt wearing methods of ready-made shirts but showed no difference in purchase intention of custom-made shirts. Fatness and body type were proved to be important for wearing shirts and it was assumed that there were socio-psychological reasons for the custom-made shirt purchase. Finally, the groups by the experience of purchasing custom-made shirts showed no difference in shirt fitness and shirt wearing methods of ready-made shirts but showed difference in purchase intention of custom-made shirts. This meant that purchase of a custom-made shirt stimulated another purchase. Therefore, shirt brands should focus on the first purchase of custom-made shirts.