MacLeay had quite an eye for detail, judging by some of the finer points of his paintings. But the thing is, he didn't just do this in one of his paintings. I'd say that the majority of his Highlander portraits where plaids are worn around the chest are depicted like this. The tartan pattern is square/in-line with the cloth across the chest, but diagonal at the draped length with the fringed edge visibly coming down next to the arm, usually in a wavy manner. Here are a few more examples below. Either he got it wrong on all his paintings, or it was commonly worn this way. And as you can see, regardless of how the plaid is attached at the shoulder (or not), the draped end consistently appears diagonally with cascading fringe. There's got to be a trick to doing this.
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