A wearable device charging system comprising a base station and a wearable charging unit. The wearable charging unit configured to couple with, and charge, a wearable item while the wearable item is in an as-worn position. The wearable charging unit comprising a housing, a battery, and a charging system. The charging system may comprise an inductive charging system or a conductive charging system. The base station including a charging system for charging the wearable charging unit and a power input for coupling with an external power supply.