Was thinking about this a little bit ago. It just dawned on me that most mob guys in the modern era grew up in areas of the city where the style of dress all through high school was influenced by rappers and hip hop. These guys like Peter Pan don't really know any better. Lets be honest, the mob isn't recruiting kids who grow up in the Hamptons and dress in designer clothing that would be labeled as "preppy" by city kids. The kids in the city dress to fit in and thats why you see them dressing like shit.