The present disclosure is generally directed to headwear and, more particularly, to headwear, including hats, visors, head wraps, head ties, bandanas and the like, that include interwoven gripping fibers, such as rubber threads or other materials having increased gripping or frictional forces beyond that of the materials from which the headwear are typically fabricated, integrated into the headwear and positioned to engage the skin and/or hair of the wearer to improve the retention of the headwear when worn during physical activities.