An ear tip is disclosed that comprises an annular flange having a first end tapering downwardly to a second end and having a non-circular lateral cross-section generally in the shape of an oval. The annular flange has a varying wall thickness from a first set of opposite sides of the annular flange to a second set of opposite sides of the annular flange. An inner body extends internally from the first end within a hollow interior defined by the annular flange toward the second end. An acoustic channel extends through the inner body, where the annular flange at least partially occludes an ear canal from ambient noise and creates at least a partial air seal in the ear canal and the acoustic channel is configured to allow the passage of sound into the ear canal when the inner body is connected with a sound source.