Face masks are an important way to combat the COVID-19 pandemic. However, the prolonged pandemic has revealed confounding problems with the current face masks, including not only the spread of the disease but also concurrent psychological, social, and economic complications. As face masks have been worn for a long time, people have been interested in expanding the purpose of masks from protection to comfort and health, leading to the release of various “smart” mask products around the world. To envision how the smart masks will be extended, this paper reviewed 25 smart masks (12 from commercial products and 13 from academic prototypes) that emerged after the pandemic. While most smart masks presented in the market focus on resolving problems with user breathing discomfort, which arise from prolonged use, academic prototypes were designed for not only sensing COVID-19 but also general health monitoring aspects. Further, we investigated several specific sensors that can be incorporated into the mask for expanding biophysical features. On a larger scale, we discussed the architecture and possible applications with the help of connected smart masks. Namely, beyond a personal sensing application, a group or community sensing application may share an aggregate version of information with the broader population. In addition, this kind of collaborative sensing will also address the challenges of individual sensing, such as reliability and coverage. Lastly, we identified possible service application fields and further considerations for actual use. Along with daily-life health monitoring, smart masks may function as a general respiratory health tool for sports training, in an emergency room or ambulatory setting, as protection for industry workers and firefighters, and for soldier safety and survivability. For further considerations, we investigated design aspects in terms of sensor reliability and reproducibility, ergonomic design for user acceptance, and privacy-aware data-handling. Overall, we aim to explore new possibilities by examining the latest research, sensor technologies, and application platform perspectives for smart masks as one of the promising wearable devices. By integrating biomarkers of respiration symptoms, a smart mask can be a truly cutting-edge device that expands further knowledge on health monitoring to reach the next level of wearables.