20. Ruff Ryders
Years Active: 1998-2010
Key Members: DMX, Jadakiss, Styles P, Sheek Louch, Drag-On, Swizz Beatz, Eve, Grizz Roc, Flashy
Elements of Style: Coordinating jerseys, Dogs, Timberlands, Workwear
As the name suggests, the double-R crew was not about fancy designer labels. How tight was this crew's jersey game, though? They made athletic gear look super dope. Whether it was the black hockey jerseys with the striped sleeves and silver "R" on the front, or the personalized football jerseys with the number "88" on it and everyone's name on the back, they were fresh as hell whether they were riding motorcycles or ripping a stage.