A deformable ear tip comprising: an annular inner ear tip body having a sidewall extending between first and second opposing ends thereby defining a sound channel through the ear tip; an annular outer flange integrally formed with and surrounding the first end of the inner ear tip body and extending towards the inner ear tip second end forming an air gap between the annular inner ear tip body and the annular outer flange along a portion of a length of the ear tip, wherein the outer flange comprises a first material having a first durometer and is sized and shaped to be inserted into a human ear canal; and an inner flange integrally formed with the inner ear tip body and comprising a second material having a second durometer less than the first durometer, the inner flange body extending from a location along the inner ear tip body between the first and second ends towards an inner surface of the outer flange body.