A wireless earbud system includes a first earbud assembly and a second earbud assembly. Each of the first earbud assembly and the second earbud assembly include a housing, an audio driver disposed within the housing, and a wireless receiving unit operatively coupled to the audio driver. The wireless receiving unit is configured to receive a wireless data signal and drive the audio driver based on audio data transmitted in the wireless data signal. The wireless earbud system may also include a tether with a first end and a second end. The first end of the tether is configured to removably couple to the first earbud assembly by a first detachable connector, and the second end of the tether is configured to removably couple to the second earbud assembly by a second detachable connector. Methods also relate to the wireless earbud system.