An eartip, comprising: a compliant eartip body having an attachment end and an interfacing end opposite from the attachment end, the eartip body comprising: an inner eartip body having a sidewall extending between the interfacing end and the attachment end, the sidewall defining a channel and having a first thickness near the attachment end and a second thickness different from the first thickness at the interfacing end; and an outer eartip body sized and shaped to be inserted into an ear canal and extending from the interfacing end, the outer eartip body extending toward the attachment end of the eartip; and a rigid attachment structure coupled to the inner eartip body at the attachment end, the attachment structure having an inner surface and an outer surface, and comprising: an upper region interfacing with the sidewall and defining discrete through-holes extending from the inner surface to the outer surface of the attachment structure; a lower region below the upper region where the inner surface defines a plurality of recesses (345a-b) positioned around the lower region; and a mesh extending across the channel and into the upper region; wherein a portion of the inner eartip body extends through the through-holes from the outer surface of the attachment structure to the inner surface of the attachment structure and forms an interlocking structure. a compliant eartip body having an attachment end and an interfacing end opposite from the attachment end, the eartip body comprising: an inner eartip body having a sidewall extending between the interfacing end and the attachment end, the sidewall defining a channel and having a first thickness near the attachment end and a second thickness different from the first thickness at the interfacing end; and an outer eartip body sized and shaped to be inserted into an ear canal and extending from the interfacing end, the outer eartip body extending toward the attachment end of the eartip; and an inner eartip body having a sidewall extending between the interfacing end and the attachment end, the sidewall defining a channel and having a first thickness near the attachment end and a second thickness different from the first thickness at the interfacing end; and an outer eartip body sized and shaped to be inserted into an ear canal and extending from the interfacing end, the outer eartip body extending toward the attachment end of the eartip; and a rigid attachment structure coupled to the inner eartip body at the attachment end, the attachment structure having an inner surface and an outer surface, and comprising: an upper region interfacing with the sidewall and defining discrete through-holes extending from the inner surface to the outer surface of the attachment structure; a lower region below the upper region where the inner surface defines a plurality of recesses (345a-b) positioned around the lower region; and a mesh extending across the channel and into the upper region; an upper region interfacing with the sidewall and defining discrete through-holes extending from the inner surface to the outer surface of the attachment structure; a lower region below the upper region where the inner surface defines a plurality of recesses (345a-b) positioned around the lower region; and a mesh extending across the channel and into the upper region; wherein a portion of the inner eartip body extends through the through-holes from the outer surface of the attachment structure to the inner surface of the attachment structure and forms an interlocking structure.