Stem holders are attached to opposing sides of the headwear crown, each forming an opening extending from its front edge to its back edge. The front and back edges of each stem holder may be partially attached to the crown such that the opening is larger along the front than along the back. At least a portion of the opening may be angled downward from front to back. For brimmed headwear, a raised flair may be positioned on the brim to create a pocket between it and the crown. For brimless headwear, the raised flair may be attached to the front of the crown to form a pocket between it and at least a portion of the crown. In either the brimmed or brimless configuration, the lens portion of the glasses will rest in the pocket when the stems of the glasses are inserted into the stem holders.