Abstract: Portable ear-worn acoustic devices having a wingtip anchor for improved anchoring for active users and to accommodate a wide range of ear sizes and shapes are provided herein. Such acoustic devices an include an earbud device body and a wingtip anchor that extends from an outer face of the device body. The wingtip anchor can include a base portion and a protruding portion that extends upwards and is angled or curved inwardly so as to engage the upper concha of the ear. The wingtip anchor can be flexible so that engagement of a distal portion of the anchor exerts an inwardly directed spring force on the device body to maintain the earbud device body within the ear. Such acoustic devices can further include a multi-function button that is integrated with the wingtip anchor such that the base portion of the wingtip anchor is a faceplate for the multi-function button.