Well when he first started doing it as a heel gangsta rapper it actually fit his character's image.
He just never updated it upon turning face because he's just this Poochie-esque amalgamation abomination of a half-dozen "cool" character traits he's picked up over the years.
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Thank you, Eddie Guerrero.
http://www.wwe.com/f/styles/photo_large/public/photo/image/2012/04/33_Moscow_04112012jg_02128.jpg