Ah, the ingenuity of the Great White North rears it head once again!
Taking the Threadless "community t-shirt aspect" and bringing a face to it is Toronto-based Joy Apparel, who urge you to "wear the world on your heart."
Actually, it's way more interesting than that. What these guys do is sell you a t-shirt with a hand-drawn portrait of a random stranger on it (these portraits are very well done, and well worth wearing).
To keep the community growing, at the time of your order, you upload your own headshot, which is converted into a hand-drawn portrait, which is then put on the t-shirt that some other random stranger buys. And then...well, you get the drill. (By the way, that's Kristina Ferraro above and my namesake, Lucious Andy, below.)
What makes this even more endearing is that Jeff Woodrow, who conceived this idea, donates 5% of profits to a different charity every month, and a la Sally Struthers, packs each t-shirt with a card that tells you all about the person emblazoned on your (sweatshop-free!) garment.
Great concept, and indeed spreads the warmth, but I think that Jeff's only scratching the surface with this one. Just think what could be done if you could harness the process for mass gatherings of people where t-shirts are sold, a la music festivals, political rallyes or street parties. The meet-and-greets could be more entertaining than the events themselves.