It doesn't seem like a money issue to me. I regularly go to a a variety of secondhand stores around here and pick up decent quality fleece pullovers, wool sweaters and pants, for next to nothing.

The other option is to post an ad on Craigslist of Kijiji and get a ton of appropriate stuff for free. There's always a way.

I think it goes deeper. I think being cold and wet, and having no warm building or vehicle to go to, is so far from their experience that they just can't imagine it.

You can talk all you want, but a lot of people don't really believe something until it actually bites them. Teenagers doubly so.

Perhaps the way to teach fabrics and properties (which rates alongside water as the bedrock of survival around here) is to show up with all sorts of donated wool and fleece stuff. Give them the background principles, and when they start to really freeze, let them choose stuff or even cut stuff up with crash scissors to make hobo/survivor clothes. The sleeve off a fleece/wool pullover makes an effective toque plus a muffler handwarmer or sock, etc. Actually, this could be a lot of fun, sort of a teambuilding exercise, since everybody dresses kind of the same, and logos don't matter.