Up until very recently, I wouldn't BUY any apparel with firearms-related stuff on it, but if it came into my possession, and it fit, I would wear it. Since, why in the hell not, it's clothing, and I now own it, so I might as well wear it.
When I started my webshow though, I did order a bunch of 7.62 design shirts, and some other similar shirts basically as costume for my webshow persona, and I do wear them (as opposed to keeping them in a special box for webshow costumery or such).