Abstract: An orthotic insert for a high-heeled shoe may have an asymmetrical heel cup including a depressed central region configured for a heel of a wearer. Features including an elevated medial-side surface along a medial side upper surface declining toward the central region, and a generally longitudinal lateral-side elevation along an upper lateral edge of the heel cup may be configured to provide a predetermined supported calcaneal angle for a wearer, wherein the angle is offset from vertical. An anterior retention structure configured as a rounded hump extending across an anterior region of the heel cup, generally transverse to the elevated medial-side surface, with a middle portion of the rounded hump curved laterally away from a center of the heel cup may be included to prevent anterior calcaneal movement relative to the heel cup.