Wireless communications system providing mobile device authentication bypass based upon user-wearable security device and related methods

A mobile wireless communications device for use with a user-wearable device comprising a clasp having an open position and a closed position, a first wireless security circuit, and a first controller coupled to the clasp and the first wireless security circuit, the mobile wireless communications device comprising:

• a portable housing;
• at least one input device;
• a second wireless security circuit carried by said portable housing and configured to communicate with the first wireless security circuit when in close proximity therewith;
• and
• a second controller carried by said portable housing, coupled to said second wireless security circuit and said at least one input device and configured to
• enable at least one mobile wireless communications device function based upon receipt of an authentication code entered via said at least one input device, and
• bypass entry of the authentication code and enable the at least one mobile wireless communications device function based upon a communication from the user-wearable device and a position of the clasp.