At the turn of the millennium, hip-hop headgear was certifiably out of control. In this video alone, there are fitteds, visors, du-rags, headbands, and whatever the fuck type of towel contraption Jay-Z is wearing. (Is that a T-shirt? People were wearing T-shirts on their head around then.) Headbands in paricular went hand-in-hand with the sporty look of the era, and lest we forget, only a square wears his headband the correct way. The logo should be upside down, located anywhere but front and center, and preferably over your ears or barely hanging on. It seems like dudes were really just uncomfortable with showing their full head of hair for a minute there. A nation of impressionable youth followed suit.
18. The ROC with the headwear smorgasbord in "Do My."