Conformable sealing eartips having ribs formed on an interior surface of one or more eartip flanges are provided. The eartip may include a body and one or more flanges. The body may include an ear insertion end, an earphone insertion end opposite the ear insertion end, and a central opening extending between the ear insertion end and the earphone insertion end to form an inner sound channel through the body. The one or more flanges may extend from the body and may include an outer sealing surface and an inner surface. At least one of the one or more flanges may include a plurality of ribs protruding from the inner surface of the at least one of the one or more flanges.