The attire of businesspersons has a significant impact on their social status and career. In accordance with the norms of the work place, the types of office attire are diversified. This research was conducted to determine the relationship between the work role of men and their attire, and how satisfaction with their work attire influences their job satisfaction. This study classifies work attire into three categories: uniform, suit, and freestyle. Data from 268 respondents were analyzed, and four work attire satisfaction factors were extracted: symbolic, quality, role function, and aesthetic factors. The group members wearing uniforms displayed a high level of satisfaction with regard to symbolism, role function, and quality; those wearing suits displayed a high level of satisfaction with regard to aesthetics; and those wearing freestyle displayed a high level of satisfaction with regard to role function and aesthetics. Overall, satisfaction with work attire was the highest in the freestyle group. For people wearing uniforms and suits, symbolism, quality, and aesthetics had a significant influence on overall satisfaction, whereas for those wearing freestyle, symbolism had a negative influence and quality had a positive influence on overall satisfaction. To conclude, work attire satisfaction had a greater effect on the job satisfaction of the men in uniforms and suits than on those wearing freestyle.