27. Biz Markie
Approximate Weight: 255 lbs.
Biz Markie has always looked cool. Whether rocking a hat with his name on it in iron-on Cooper typeface (decades before OFWGKTA had co-opted the font for its merch), or wearing a camo parka, he kills it on the regular. The fat chains, Champion sweatshirts, and quilted jackets he rocked in the '80s were beyond dope. It's tough to look good, but when your style can hold its own against Big Daddy Kane, one of the GOATs, it's safe to say you're doing it right.