Most guys keep a pair of work boots about three months too long. The boots feel fine because you got used to feeling worse, slowly, over a hundred days. Five signs the boot is done. If you've got two or more of them, retire it.
Sign one — the heel has rolled to one side. Stand the boots flat on a level floor and look at them from behind. If the back of the boot leans inward (toward each other) or outward (away from each other), the heel cup has collapsed and your gait is now compensating for a misaligned foot. Knee and hip pain follow.
Sign two — the welt is gone. The welt is the strip of leather where the upper meets the sole. On a Goodyear-welted boot, that's where the sole stitches to the upper. If you've worn through the welt itself, a resole now requires reconstruction work that costs more than a new pair. You missed the window.
Sign three — the insole is permanently compressed under the ball of your foot. Pull the insole out. If there's a crater under the ball that doesn't bounce back when you press it, the boot is no longer cushioning that part of your foot. Replacing the insole helps temporarily, but the boot's own footbed is also compressed underneath, which means the impact is going straight to your foot.
Sign four — the toe box has collapsed downward. Look at the boot from the side. The top line of the toe should be roughly horizontal or curve gently upward. If the toe has dropped — sagging downward where there used to be height — the toe box has lost its structure. Your toes are now hitting the inside of the boot with each step, and over time that's going to bruise the nail bed and cause toenails to die.
Sign five — water comes in. Drop the boot in a sink of water for ten minutes. Take it out. If the inside lining is wet, the boot is no longer waterproof. For some trades that's fine. For roofers, plumbers, anyone who works wet — it's done. A wet foot for eight hours a day causes skin breakdown, blisters, and the kind of foot fungus you spend the rest of your life trying to get rid of.
Bonus sign — you've stopped wearing them by choice. There's a reason you reached for the other pair this morning. Your foot knows.
We resole what's worth resoling. We tell you when it isn't. Bring the old pair in when you come for the new one.