I found this shirt recently. A 100% wool pop-over half zip in red buffalo plaid, made in the USA by Chippewa, probably in the 70's:
I'm a city guy, and I will likely never find myself cutting firewood on a cold day.
I'm (more than) a bit of a fop. For me, it's more about being overdressed....jackets, pocket squares, ties when they aren't required, a million pairs of impractical shoes and so forth.
This shirt is the absolute jams. I saw it, it called my name, and now it's mine. Will I wear it with the full kit of L.L.Bean accesories? Probably not. Will I wait until some weird outfit presents itself to me that absolutely requires this shirt? You bet!
It doesn't "go" withe the rest of my wardrobe. It doesn't "go" with my lifestyle. It also doesn't matter. Because I like it, and I plan to wear it with all the confidence and aplomb I can muster.
So I go with my gut, I buy the damn lumberjack shirt, and I'll figure out how to wear it when the time is right. That's how I like to think about style. Sometimes, you gotta throw a curve ball...keep 'em guessing.