As society ages, wireless body area networks (WBANs) are expected to increasingly improve the quality of life of the elderly and disabled. One promising WBAN technology is human body communication (HBC), which utilizes part of the human body as a transmission medium. Communication between head-mounted wearable devices, such as hearing aids, is a potential HBC application. To clarify the HBC transmission mechanism between head-mounted wearable devices, this study analyzes the input impedance characteristics of the transceiver electrodes, transmission characteristics, and electric field distributions around and through a detailed head model. The investigation was performed via an electromagnetic field simulation. The signal frequency had less effect on the transmission characteristics and electric field distributions at 10, 20, and 30 MHz. However, the transmission mechanism between the head-mounted wearable devices was influenced by the number of electrodes in the transceiver. Moreover, the transmission characteristics between two-electrode transceivers were improved by impedance matching. Finally, the availability of the proposed system was evaluated from power consumption and human safety perspectives.