Honestly, seeing a friend just wear it out to a regular barbeque did the trick for me. He had on a nice flannel with dark jeans and clean boots, looked totally normal. It kind of broke that mental link to just being for chopping wood. After that, I tried a thinner one over a t-shirt and it just clicked.
It's like watching any trend hit the mainstream. You see it first in one group, then it takes years for everyone else to catch up. I guess some people just don't pay attention until something's everywhere.