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short hair here.
the key to surviving for a long time in the woods is to keep it simple, and keep your options open.
short hair can be cleaned in no time at all, and in a pinch even hand soap does the trick.
if you are afraid of getting cold because you have short hair you can just buy a hat or a beanie of some sort, you can even get one of those silly hats with hair extensions to keep your neck warm, add a scarf to it and you are golden.
now some of you might ask "why would I do that when I can grow my hair out for free?"
the simple answer is, you can't cut off your hair when you are in the middle of nowhere unless you have a friend who is also a barber.
if it gets too hot while you are walking, but its too cold when you are camping for the night (which is often the case) you are better off with a beanie or hat that you can take off while walking.
now if you have nowhere to be and nothing to do, having long hair to keep clean and brush might help you stay sane by giving you something to do, and to keep track of, but that's about the only benefit I can think of