With the increasing maturity of mobile networks and big data technology, smart wearable devices (SWDs) are regarded as a new technology trend following smartphones. Especially during the COVID-19 pandemic, the increase in telework and the growing interest in self-health monitoring have greatly promoted the market growth of SWDs. This study aimed to investigate the factors affecting the continued use of SWDs. A cross-level analysis model that integrates technical characteristics, gamification theory, perceived value theory, and network externality was constructed. A hierarchical linear model was employed to evaluate the data and test it against the hypotheses. The empirical results showed that, at the individual level, gamification enhances users’ value perceptions. Users pay more attention to rewards in gamification than to competition. Rewards were also found to effectively promote the users’ value perception and increase the intention to continue using the device. At the group level, the effect of network externality significantly influences the intention to continue using SWDs. Moreover, SWDs are associated with the phenomenon by which consumers conspicuously display and highlight their own characteristics, and this attribute is also a crucial factor enticing consumers to continue using SWDs. Developers should therefore establish clear product positioning and strengthen interactivity as early as possible to build a loyal customer base.