The crowd context-based learning process via IoT wearable technology [IoTW-driven Crowd context-based learning (CCBL)] is a new learning paradigm that integrates Technological Cybergogical Content Knowledge (TCACK) based on connectivism, cognitive tools and information processing theories to promote digital health literacy. In this study, the IoTW-driven CCBL was designed by incorporating content, cybergogical, and technological elements, which can become a sustainable solution in educational settings during the global COVID-19 pandemic. The researchers collected qualitative data by confirmatory focus groups from 12 experts who hold doctoral degrees or equivalent and have at least 3 years of relevant experience. The results of these studies found that the IoTW-driven CCBL involves three specific learning contents (healthcare, disease prevention and health promotion); five dynamic learning steps (context-aware alerting step; observing and questioning step; social information-seeking step; action step; and self-reflection step as all cognitive tools embedded in IoTW devices help promote all digital health literacy components); and four cognitive tools (notification tool; communication tool; searching tool; and monitoring tool). The IoTW-driven CCBL will allow learners to respond to real-life situations by utilising IoT devices to access, apprehend, appraise and apply health information from digital technologies in daily life for well-being, especially in educational settings.