Then again, Dean was probably going mostly for the Man With No Name look and just grabbed whatever mostly fit

Actually, I read somewhere that that was indeed the look that they were going for - an attempt at Man With No Name.

I think Jensen said at one convention that the first hat was actually an "Australian" style cowboy hat, if that's true, then that's the biggest mistake in Dean's costume in my eyes.

But yeah, not much they can do about the cleanliness either way. ;)