Nonprofit organizations operate charity retail shops to raise the necessary funds to enable them to carry out their primary charitable purpose. This research conducts six case studies in the charity retail sector to develop the charity retail branding strategy decision pathway to link (a) "why" nonprofit senior managers choose different types of charity retail branding strategy and (b) "how" they conduct legitimation strategies accordingly to attain brand legitimacy. In the course of developing our argument, this research extends the theory of brand architecture and brand legitimacy by articulating their application in third sector retailing practice. These findings will also be useful for senior managers when making branding decisions and designing legitimation strategies to attain brand legitimacy.