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Underwear and socks are tossed the minute they get a hole or the elastic gives.
Undershirts get replaced the minute they have a hole or the pits get hard from sweat and deodorant and will not wash out.
Overshirts will get worn until they are faded out completely, thin, or have holes.
Pants will be worn until they become stained (oil, grease, blood) or ripped (sometimes it is the knee, sometimes it is at the ankle, once had a seam burst from ankle to ass). Depending where the rip is (the knee) I might patch the pants and keep them rolling as work pants. If they are stained but still in good shape they will be relegated to "work" pants.
Shoes will be worn until just before I can see my toes poking out of the front of them.
I won't buy fitted caps anymore because they just stop fitting after a while so they get tossed. Snap back caps will be tossed after they lose their shape or become overly stained. I have thrown away hats after a particularly bad run of games but I'm not sure my superstitions are relevant to the question.
/edited to add that I keep a relatively small wardrobe meaning that the often washing leads to them wearing out sooner and, thus, me having to replace them more often than the average user
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