E-commerce has provided an opportunity for organizations to prosper. Online shopping is regarded as a new technology adoption of Web site functionality that firms provide. Our model examines the impacts of a Web site’s functionality on online shopping behaviors from perceived benefits (usefulness, ease of use, and playfulness) and perceived risks (trust and familiarity) perspectives. We expect to predict online purchases more accurately by combining consumer-perceived benefits and risks for different consumer lifestyles. This paper helps examine online shopping behaviors more thoroughly from different sides, such as IT functionality, design, and marketing strategies, to better satisfy specific consumer needs.