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I have old school felted wool shirt and field pants and I fucking love them. There's nothing more comfy for hiking on a crisp fall day.
However, as soon as rain clouds appear or I get above the snowline, the synthic rain gear and gaiters come out.
Because, speaking from first hand experience, hiking in saturated wool suuuuuuucks. Yeah, it still insulates when it's wet, but that doesn't mean it isn't heavy and uncomfortable (and chaffy).
Obviously people went /out/ with wool and leather everything in the past, and you certainly still can do it today. But they didn't do it to be macho or fashionable, they did it because those were the best available materials at the time.
So as long as you're cool with the limitations of whatever you are wearing, you'll enjoy going /out/ in it.
