>>10544677Newsboy caps/driving caps are fine but not everyone can pull them off. It depends on what you look like, not the person modeling the hat in the photo.
But really who gives a fuck? If you like a hat, wear it. I wear a suit and a Yeti Cooler baseball hat to work most days in a Fortune 500 company because my hair just doesn't style well most days. Nobody has ever said anything to me. I'll take it off if I'm meeting important people, but it goes right back on the second they leave.