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As the owner of several western hats, I'm curious about Jeff Bezos' hat. What's the story behind it? It does not fit him well. He obviously has the money to have whatever kind of crafted, perfectly styled hat he wants. Maybe something from his family?

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Having spent time supporting these sorts of live / PR events, there's a non-zero chance that this was brought in last minute by an underling.

Iirc this is in Texas so local affectation probably?

He's spent time on ranches, so probably knows how they're supposed to fit; this one's practically resting on his ears.

I'm curious if it's a hat that means something to him for some reason.

That sounds basically like what I'm saying: He owns a ranch and occasionally spends time there because part of the reason the rich often have these ranch properties is to cosplay part of the independent west/cowboy dream. He probably rarely wears one and basically only does so when he's on this ranch as part of the aesthetic.

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