Although biofeedback systems have been used to improve balance with success, they were confined to hospital training applications. Little attempt has been made to investigate the use of in-shoe plantar force measurement and wireless technology to turn hospital training biofeedback systems into wearable devices. This research developed a wearable biofeedback system which detects body sway by analyzing the plantar force and provides users with the corresponding haptic cues. The effects of this system were evaluated in thirty young and elderly subjects with simulated reduced foot sensation. Subjects performed a Romberg test under three conditions: (1) no socks, system turned-off; (2) wearing five layers of socks, system turned-off; (3) wearing five layers of socks, and system turned-on. Degree of body sway was investigated by computing the center of pressure (COP) movement measured by a floor-mounted force platform. Plantar tactile sensation was evaluated using a monofilament test. Wearing multiple socks significantly decreased the plantar tactile sensory input (p < 0.05), and increased the COP parameters (p < 0.017), indicating increased postural sway. After turning on the biofeedback system, the COP parameters decreased significantly (p < 0.017). The positive results of this study should inspire future development of wearable plantar force-based biofeedback systems for improving balance in people with sensory deficits.