I'd go to Landsend.com and buy him a fleece 1/2 zip up shirt of some sort. All men can use something like that. (unless, of course he lives in a warm climate)
How about a stripper!? Sorry, but that's the first thing I thought when I was ready your post.
Seriously though, is there some sort of "uniform" that he needs to wear while bartending? Maybe specific colored polo shirts or a shirt and tie? Then again, cash is always the right color and size and I don't know anyone who doesn't like cash.
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