Devices for attaching earpiece to a user's ear are described herein. In one embodiment, an earpiece that is removably attachable to an ear of a user can include a housing that has a proximal end portion and a distal end portion. A transducer may be positioned, for example, at the proximal portion of the housing, and a retention member can be elastically coupled to the distal portion of the housing. The retention member and the housing can be configured to compress a portion of the user's ear therebetween in a manner that positions the proximal end portion of the housing in a vestibule of the ear adjacent an entrance to the auditory canal of the user's ear when the earpiece is attached to the user's ear.