If I see a man who is in his later 30-50s all decked out in gangsta wear and he lives far away from any major urban centre and has never met a gangster in his life, I would have a hard time taking him seriously. It's not age appropriate, nor is he part of the group he is trying to emulate. Shoes are only one part of that.
I think Jennifer is right though that the biggest factor in my judgement of shoes is where they are worn. Even if you do legitimately dress to reflect a certain subculture, there are some occasions or some workplaces with a different subculture dress code which ought to be observed or it indicates a lack of awareness that could extend into other areas of a potential relationship as well.