My Desert Rat boots are the best boots I have ever had.
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sounds like you've just not found boots that fit you right, I've had pain wearing many types of shoes untile I've found the size that works be for me,
I got a pair of timberlands that are quite comfortable tho they don't last very long
Yes
I've always had Doc Martens boots for casual wear in the winter. They're really comfortable as long as you break them in by wearing them around the house for half an hour a day for a week or two before going outdoors with them.
Getting cushioned insoles might help?
I wear Doc's a lot but never in winter! They're just ice skates in disguise.
Knowing how sensitive I am, I can't imagine buying footwear I didn't think was comfortable.
I have some swedish brand boots that are pretty comfy... Wait, are we talking about rubber boots, Dock Martin's or just boot boots(for booting)? because I never wore the first two, so can't help there.
Cozy and like armor. The hard part is finding something that properly fits. I like hardened toes, and need double wide for my ogre feet and its hard to find with something that's actually good and comfortable in my size.
Get boots made for construction workers. They are on their feet and in boots all day. I got a pair of redwings a few decades ago and they were my daily walking shoes until I got a car.
Military: Danner, then Belleville
Security: Nortiv8 (see Amazon)
Field Service: Skechers Work (no,they aren't boots...just comfortable)