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Thorogood's boots: the version you keep rather than replace.
Recently seen around $284.95 — check Amazon for the current price
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Thorogood Series 8” Waterproof Work Boots, full-grain leather, waterproof, built for regular wear.
Thorogood boots are union-made in the United States with Goodyear welt construction, so they can be resoled repeatedly.
At $284.95, it sits in the bracket where paying once tends to work out cheaper than replacing something twice.