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I would wash them before getting them tailored, just to see what they'll wear like post-wash (which I assume is when you'll be wearing them, mostly). Don't want to over tailor and realize it only after you post-tailor wash. Not sure if wearing a few times is necessary, given that I don't think chinos change as much as jeans can.
I haven't altered jeans in a while -- the Bonobos I've purchased in the last year fit me perfectly, other than a hem (which I've let go and just rolled as of late... may do that sometime soon tho). I wash everything but dry clean items prior to tailoring. Never done the wear for jeans on purpose; the jeans I had altered a few yrs ago were already broken in before I realized I should get them tailored.
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