Earphone assemblies with wingtips are provided for anchoring to a user during use. A wing may extend from and between two different ends coupled to a housing of an earphone, while each of the at least one flex arm may extend along the wing. At least one flex arm may be rigid enough to prevent at least a portion of the wing from bending out of a plane of the wing such that a portion of the wing may maintain a functional position under and/or behind at least a portion of a crus of an anti-helix of a user's ear to anchor the earphone to the user's ear during use, while at least a portion of the wing may be flexible enough to provide comfort to the user's ear.