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A long time ago, I had a pair of Hi-tec Magnum Tankers, which were pretty much the greatest show I've ever worn. Outdoors, urban, work, casual, whatever, they were fucking great everywhere, and I wore them to their inevitable death.
My favorite part about these (besides their comfort, obviously) was the loose upper they have. Hi-tec doesn't make them anymore, they're impossible to find used or new old stock, so I'd kill to find a good new boot that has that same style, but every time I go looking I just can't find something that fits the bill.