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I don't think it really matters...As long as you always have a clean pair to put on.
I only have 5 boxer shorts, I just make sure that i always have atleast 2 or 3 clean...I always wash my boxers, socks and towels more than my pants & shirts. I can wear my clothes more than once...But I won't wear boxers more than once or socks.
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"To win any battle, you must fight as if you were already dead" -Musashi
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