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Aviator & Trapper
When airplanes were first invented, they were open to the wind! Pilots needed a hat to keep their ears and heads warm in the chilly conditions (and have a place to put their goggles when they weren't in use) so the aviator hat was born. Usually made of leather for extra protection, even as planes became fully enclosed the aviator hats were worn through WWII until they were replaced by caps for commercial pilots and helmets for military.
Trapper hats are a similar style to the aviator, usually made of leather or wool, but more often lined inside with shearling or animal fur for added warmth. They are derived from the Russian ushanka, and were made popular for winter by fur trappers who worked out in the snow.