Coming from someone who will soon be making the same journey, I would suggest you wait until you see what he is issued. I was very surpised to see waht the Marines going over there are issued. I am not sure how it works in the Army.
I would agree on/suggest a few things:
Phone card
Reading material
MP3 player
Pancho liner
awesome socks
extra razors, and other hygene gear. If he is on a base, it will be easier to get these things, but if he goes out, he will need extra.
Pictures from home
A good knife
A good multi-tool.
I wouldnt even consider body armor from a private vendor. He will be issued that by his command. Everyone is getting it now. Plus the stuff you buy may or may not fit with his gear.
Winter is still cold over there, especially at night, so a good pair of gloves will make him money over there, as military gloves are still pretty bad.
All the other suggestions are right on the money! Let him know that I said good luck and my prayers go with him.
garrett
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On occasion of every accident that befalls you, remember to turn to yourself and inquire what power you have for turning it to use. - Epictetus