If it sang or wiggled its tail like the singing bass i would buy that fish hat in an instant

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A soviet made ushanka with a hammer and sickle pin in the center

That chaperon is fucking great. Doubt I could pull it of though.

I would gladly wear the Phish or Bulls hats. I don't think I could pull the rest off but they are very cool.

Beanie for when it's chilly enough to make my ears hurt, baseball cap with a punk patch for days it's too sunny/hot or driving the convertible, helmet when biking. Otherwise, I don't much like hats

My taste in hats is garbage except for the bowler that I wore as a teenager and the Union Army cap I wore like a snapback in my early 20s