With the recent development of technology for wearable devices, user experience design is considered as the important design strategy. The purpose of this study is to conduct practical user experience design for smart headwear for bike user. To find smart headwear contents, the user needs and pain points were extracted from the user research. In developing the user experience (UX) design elements, persona and user journey map were created to provide differentiated experience contents for bicycle user. In this study, smart headwear through UX design process could provide the guidance for route during the cycling, coping with accidents, and bicycle trip. The smart headwear development with UX design process could suggest the UX content direction and the business success model. This study could be helpful to establish the UX strategy for smart devices for bicycle users.