Certain embodiments provide a conformable eartip. The conformable eartip includes a round flange and a core. The round flange includes a sealing surface for mating with walls of an ear canal. The round flange extends from an insertion end to an opposite end of the conformable eartip. The sealing surface is tapered from the opposite end toward the insertion end of the conformable eartip. The core is joined to the round flange at the insertion end of the conformable eartip. The core extends from the insertion end to a base of the core toward the opposite end of the conformable eartip. The core includes a channel extending through the core from the insertion end of the conformable eartip to the base of the cor. In various embodiments, the conformable eartip provides an elongation ratio of at least 1.4 and/or a compression ratio of at least 2.0.