Consumers struggle to find clothes that are fit. This is a problem that has been accentuated with the increasing online sales. It is the largest contribute to sales returns and make customer return about every third item they buy. a few companies have provided a number of solutions to the fitting problem. We investigate a new approach, called “Figuracy”, where people get suggestions on the garments that are fit by crowd sourcing their existing clothing items and then matching wardrobes among members in the community.We did an initial user study on the system. The results show that this idea gained great interests among participants. However, they expressed their uncertainties towards how the system would work. Although the application failed to provide new recommendations based on matching, the user study allows us to see the feedback of the potential users so that we could improve the system. In all, the study provides an example on how to investigate critical topics in online fashion through the so-called design research.