An article of headwear to treat an infant's persistently maintained head position with respect to rotation about the cranial-caudal (head to toe) axis, seen in conditions such as plagiocephaly (baby flat head) and torticollis (wry neck). The headwear both permits and encourages an infant with a preferred head position to volitionally turn his or her head in several positions thereby promoting head and neck rotation and development of a naturally shaped cranium, thus treating or preventing torticollis and plagiocephaly respectfully. The infant headwear generally includes a head receiving member and positioning guide member. The head receiving member is placed on the infant's head and allows strategic placement of the positioning guide member. The positioning guide member increases the ability of the infant with a flat region to turn his or her head by re-establishing a round contour, and selectively increases cutaneous pressure in order to balance the variables influencing the infant's preferred head position.