I'd buy one! I like the idea of being able to download the design for a fee. That way you can choose what you want to put it on, T Shirt, Sweatshirt, etc.
It's not a bad idea, though I am a bit skeptical that enough people would be willing to buy the shirt to make it worth the trouble. That being said though, I do know a few places where I can get decently-priced custom tshirts. The only problem would be coming up with the design.
If you ran a contest and got members to design the image to go on the t-shirts, you could then put up a poll. You could then choose out of the top favourites yourself. Also, you could do a poll and see how many people would be interested in buying a t-shirt, or get them to put their names down for one and not order them until you have a decent number of people that would like to purchase one. That is if you wanted to go ahead with it. Though I would be skeptical about it until you have a larger member base that is rather active. At the moment, we do have a large member base, but not a overly large active member base as yet. Maybe wait it out until a bit further down the track.