Square is a mindset and it’s got nothing to do with doing illegal shyt. A square is a modular citizen that fits neatly into the box assigned to them by society. They follow all rules whether they’re in their best interest or not. Their personalities lack any intrigue or edge. Their lives are routine and they try their hardest to not offend anybody with their actions and opinions. They are underdeveloped in many ways. They are not the real thing. Society wants you to be a “square” because nothing scares them more than someone who doesn’t need them.
Being a “bad boy” is about not relinquishing your masculine attributes to society. You don’t expect the police to protect you, so you protect yourself. You don’t expect “the man” to give you a job, so you provide for yourself. You don’t expect the system or its schools to teach you, so you learn from the streets, the world, and from experience. It’s close to being a renaissance man but it’s mainly about being a man. You’re called a “bad boy” because a “model citizen” is modular and doesn’t develop himself fully; they just fit into the narrow role designated for them by society, like a “square.”