Rechargeable wireless earphone systems and charging cases are disclosed. The rechargeable charging case, which doubles as a storage case for the earphone components, includes externally accessible charging ports adapted to charge the rechargeable battery contained therein as well as for charging other electronic devices. The earphones are configured such that they may be used even when charging or when the earphone system battery is depleted. An alignment and positioning mechanism is provided to align and electrically connect charging contacts of a controller housing of the earphone system with charging contacts provided in the charging case to better secure and facilitate the charging process when the controller is received within the charging case. Reversibly detachable ear hooks and ear canal plugs are uniquely designed and configured to be independently attached to the earphone housing and compliantly adjustable to the desired shape for user comfort. The ear hooks and plugs may be configured such that the ear hooks at least partially encircle the ear plugs when both are attached to the earphone housing and either the ear hooks and/or ear plugs may be detachable from the earphone without removal of the other. Illuminated ear hooks and cable are also disclosed.