Who started it: Biz Markie
Circa: Mid-'80s

Those iron-on letters you can buy at the arts & crafts store were pretty much the precursor for modern-day streetwear. When young b-boys and b-girls wanted to rep their crew or personalize their gear, they did it themselves. Biz Markie is immortalized with his thick chain and off-kilter "BIZ" hat, done up in the recognizable "Cooper Black" typeface—a readily-available DIY font that's been appropriated most recently by OFWGKTA.