Social commerce can be briefly described as commerce activities mediated by social media. In social commerce, people do commerce or intentionally explore commerce opportunities by participating and/or engaging in a collaborative online environment. As a relatively new phenomenon first widely acknowledged in 2005, social commerce presents new opportunities to examine issues related to information/content, business strategies, management, technologies, and people's behavior. This article presents a qualitative longitudinal study which systematically examines technological features and tools in social commerce websites to illustrate their evolution and impacts on the formation of social commerce practice today and its potential future. Using captures crawled by the Wayback Machine, fifteen websites are analyzed from the year they were “born” to the year of 2010. The analyses are guided by a semi-structured checklist of expected and desired tools and features based on a literature review in social commerce. The study finds that social commerce activities appeared as early as the late 90s and that there are different approaches to incorporating social channels and social networks. In addition, the findings support a preliminary classification of social commerce websites, a realignment of the term's conceptualization and the anticipation of possible new directions for this market segment.