Clothing behavior is essential factor in the process of building one’s self-esteem and protecting one’s body. However, people with disabilities face few options when choosing appropriate clothing for their social lives in Korea. The purpose of this research is to explore clothing behavior for wheelchair users with functional, psychological, and aesthetical aspects and to analyze design factors for adaptive clothing design based on these aspects. To explore wheelchair users’ challenges and experiences in clothing behavior, qualitative in-depth interviews were conducted with five care-givers at the center for independent living for disabled people in South Korea upon IRB approval. The interview data was interwoven with indirect observation data from the top five ranked YouTube videos created by wheelchair users who are able to work and socialize. The multiple layered data was analyzed based on the three levels of coding scheme used in grounded theory analysis. As a result, five themes were emerged from the data. First, wheelchair users face problems because of diverse physical features and environmental barriers. Second, There is a lack of clothing that meets the psychological and aesthetical needs of wheelchair users to choose in their social lives. Third, there are material-related problems such as inappropriate fabric that is susceptible to contamination and prone to becoming threadbare. Fourth, wheelchair users face limitations in dressing and undressing with a diverse range of reasons. Fifth, wheelchair users do not have enough clothing options to find a comfortable fit, especially regarding patterns, details, and fabric. These factors have co-relationship for wheelchair users to improve their self-esteem and meet their aesthetical needs beyond functionality. The results showed that adaptive clothing design for wheelchair users should be considered these factors holistically in the future.