Shopping is a social activity that people enjoy doing with friends and close ones. In this paper we name such joint shopping activity performed by two or more people together as “collaborative shopping”, and investigate the possible means of carrying it out online. We start with identifying the objectives of collaborative shopping (i.e., socializing and purchasing) and propose website features (communication support and decision support) to support these objectives. Our study posits that a better fit between the shopping objective and the website feature provided results in higher process satisfaction and outcome satisfaction. This research advocates further research in online collaborative shopping and hopes to provide guidelines for website designers. We believe online collaborative shopping deserves more research attention, not only from a purely research-oriented perspective, but also for its practical potential for making online shopping a success.