Run DMC: 1988
Run DMC: another music act with a legendary image capped off by the wise addition of headwear. The trio's toppers of choice in the 1980s were Kangol fedoras, which you can still readily purchase. The rest of their proto-street fabulous look is equally minimal, striking, and painless to mirror: black or dark-hued tee paired with a fat gold chain, clean sweats, and Adidas. Carrying an appropriately oversized boombox around as an era-specific accessory is optional, but recommended for keeping it real(er).