This study develops a novel sensing system to monitor two trip-risk-related factors when walking on any surface and under any condition. One factor is the visualized plantar aspect during walking. We extended our previous system to a new wireless wearable device that also provides more stable image as well as improves the walking comfort. During walking, a plantar image is produced on a reflecting surface and captured by a camera embedded in a clog. The other factor is the minimum toe clearance (MTC). MTC is defined as the minimum distance between the ground and toe at the swing phase. Acceleration and time-of-flight sensors are attached to the plantar surface of a clog to accurately observe the MTC. The efficacy of both sensing systems embedded in the clog is demonstrated using the data obtained by experiments.