I think I see what you're talking about in some of those water colors - Day jackets with plaids wrapped around the chest. There were enough different gentlemen wearing plaids that way to make me think that that was probably not too unusual at that time. But remember, those are all historical documents, not modern fashion guides. I've never seen a plaid worn that way over a day jacket or anything similar, like an argyll jacket. The plaids were worn differently then, too. Modern pipers plaids are carefully folded and the pleats are sewn in. In the old paintings and photos, even of military pipers, the plaids are always much less carefully folded and seem to be almost spread out to cover most of the chest.

You could always try it. See how you like it and what other people think. I'd save it for cool weather, though. A wool blanket wrapped around a wool jacket may be more than you need most of the time.