Why is it so hip to wear squares? As it happens, the Scottish men have been matching their kilts and bonnets for generations, and very fine they look. So here are we, copy pasting but maybe styling it a bit different (wearing underpants at least), and I can say that we look quite fine, too. We are wearing something with tradition, but despite our best efforts we can quickly get it wrong, and can end up close to the cliche of the American tourist in a too-bright plaid jacket and a Burberry scarf/coat/pants/bag/gloves all matched together, seen a million times.
Personally, I prefer big, college like, wool coats with checked patterns. So here is fall/winter look with my favorite college coat and a dress in which my back is mostly freezing.