I own a couple of touques and a baseball cap that I wear only when I think I'm going to be spending enough time in the sun to risk heat stroke. I'd like to wear a cap around town, but old-fashioned hats like that have been pretty much completely co-opted by hipsters and greasy nerds who do not understand the concept of an "outfit," and I don't much feel like associating myself with either group.
If your hat doesn't match your shirt or jacket, you look like an idiot. That's all there is to it.
If your hat doesn't match your shirt or jacket, you look like an idiot. That's all there is to it.