It means that while you might be plenty smart (or might not be, I don't know) it means you don't know how certain things in the world works. Particularly some kinds of business sense more down to earth, or haggling, or you don't know where to go to get the absolute lowest price on anything. It could also mean that you're naive and to trusting of other people. That or you can be screwed with too easily and thus can be taken advantage of.
Basically being streetwise and street smart means a more simple, barebones level of human psychology. Forget the Freud and Junt analysis. Forget your economics degree. Forget your military strategy. Forget any kind of book smarts or fancy lernin' n' shit. It's all about knowing the basics on how people act. Watching people. Figuring people out. Like if I do this, they react like that.
That's generally what street sense is all about.
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It means you have no common sense in regard to how to survive in an urban environment. You'd do dumb sh*t that would get you into a bad situations like being mugged by a stickup kid. You're naive and would get took. You don't understand how things go down.
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It simply means you don't know the ways of the "street". For instance, many people don't realize that if you don't pay your property taxes, the city won't keep repaving your street and eventually you'll have to move. Or alternately, if you climb up a telephone pole and dive off headfirst into the street, you'll quite possibly die, or at the very least hurt your head in a bad way. These are things we all pick up as we go along.
It means you don't know the local street culture. Weather that is gangs, skater cliques, or drug dealers differs based on your location.
It isn't really an insult if you're not a person who deals with the "lower" criminal elements of society.
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