In my experience, people of every social strata sometimes do audaciously stupid things, and it's not because they get special treatment. It's often the people who have gotten in trouble the most that do audaciously stupid things the most frequently, despite experiencing past punishment.

Your observation matches what we would see if those people you speak of were just stupid for no reason and committed crimes that aren't caught as often. If a crime is only caught 10% of the time, they probably won't get caught the first few times. You can interpret that as them learning they can get away with it, but the person who just does stupid stuff for no reason will do the same thing, it isn't evidence one way or the other.

And they'd still be stupid the first time they committed the crime, before they've learned they can get away with it. And if they get convicted eventually, it was still stupid in the end. And if they don't get caught, we usually don't know about it, which makes it hard to argue that it's actually worth it for them to do these seemingly stupid crimes; we know of their failures but not their successes.