The invention is an article of headwear that incorporates a hair compression system and adjustment system for compressing one or more sections of a wearer's hair. The headwear may be formed of a crown, a compression system, and an adjustment system. The compression system includes one or more stretchable materials that form the inner layer of the crown. The compression system may compress along a horizontal, diagonal and/or vertical plane of the head of a wearer. The compression system is attached to an adjustment system often at the back of the headwear which can be attached to the crown. The adjustment system allows a user to manually tighten the compression system to a desired pressure to keep the hair of the user compressed while the user wears the headwear. The desired hair compression is capable of being regulated by the adjustment system. When the user is finished wearing the headwear, the adjustment system may be released to allow the user to remove the headwear without undoing the effects of the compression system.