There is no doubt that growth of electronic commerce (EC) on the Internet/Web is only going to accelerate even more. However, given that commerce in these environments are virtual in nature and that most consumers feel uncomfortable with this virtuality a more compelling issue is how can the EC environments be made more acceptable to consumers to approximate their real-world physical store purchases behavior. Drawing upon previous literature, this study uses the theme of “fit” between EC environment and the product type, develops four different prototype systems depicting different EC environments, and using laboratory-based experiments examines the influence of “fit” on four user outcomes. Significant support to the “fit” theory is obtained.