A cool hat? The term confuses him. He understands cool to be a compliment more so than just indicative of temperature. But to him it is just a hat. It has an aura about it, maybe. Conveys a certain image. Gives them a sense of security. But ultimately it's just a hat.

"I-- I mean I'm flattered you are asking me for fashion advice." He doesn't know what has been trending for the past century. Judging from the reaction to what the local clothing store has to offer, not flannel. But he might be a little biased, in that he doesn't really care for 'hat head' or 'hat hair' or whatever it is Malcolm is worried about.

"A knitted hat would be practical. It may get colder yet, and function is more important than form out here. We may need more blankets. Warmer coats. You are probably used to this, but I don't think Raylan finds this climate agreeable."