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I live in Chicago, and the only winter gear I own is a surplus army wool commando sweater. Been wearing the same one for 5 years now.
They are super comfy, breathable, water resistant, and warm as hell.
I've worn them down to -15F, and in 100F desert heat.
What I'm lacking are proper leggings. My thighs get cold. I wear jeans, and could use some long johns. Smart Wool makes some great ones, but they are hella fucking expensive. Good alternative brand?