If I had to wear a hat
I think my ideal hat is definitely No Hat.
But if I had to wear a hat, I wouldn't want the hat to be pointy. I feel like the natural shape of my head is simple and exquisite, and I don't want to make any extreme changes to that.
I don't love the idea of a brim, but my dad makes a good point when he talks about it being a good way to keep the sun out of your eyes. If I'm wearing a hat anyway, I might as well choose one that would provide a useful service to me.
My hat also would have to be heavy enough that I couldn't forget it was there; what's the point of wearing a hat if you're oblivious to it? On the other hand, I don't want a hat so large it hurts my neck.
If I had to wear a hat, it would have to be visually interesting. I'd want my hat to really add something to my outfit. Since geometric shapes are pretty much out of the question, the best way to maximize visual impact is likely by choosing an exciting color for the hat.
Based on all my criteria, I think my ideal hat, if forced to choose one, would probably be a hard hat, like those worn by construction workers.
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