All of this is by way of an introduction to my real topic, which is the wearing of kilts. Like building fairytale castles, kilt-wearing south of the border was popularised by the Victorian gentry who developed a sudden interest in noisily declaring a Scottish heritage. Unlike building fairytale castles, of course, almost anyone can wear a kilt and many people do with little or no meaningful Scottish connection. Kilts can be worn, with slight variations in the outfit, to white tie or black tie events, and to formal day events, and they tend to look extremely smart. Most highland outfits involve a waistcoat which, as you know, I think is almost always an improvement. In any case, the wearers usually take more care over their appearance than the average man in a tux, and they add considerably to the general variety of formal-wear at an event.
Image From Kinloch Anderson
Kilt styles, and their accompanying jackets and accessories, vary enormously and there are plenty of different options, perhaps even more than with black or white tie. I don't know nearly enough about them to attempt to explain them all; if you are unsure then taking the advice of a good Scottish tailor will be key. So long as you wear the appropriate version of highland evening wear, you should be able to be correctly dressed at any event. However, you may still wonder; should you wear one? Are you entitled to?
There aren't really any hard and fast rules. I have heard it said that a real Scotsman never wears a kilt south of the border, but this strikes me as a rule rarely observed and is, in any case, without any particular justification that I can see. Ultimately, it is up to you whether you feel you could justify yourself if, at a party, someone were to ask you why you were wearing traditional highland wear. Especially if the person who asked you happened to be a genuine Scottish Laird. If you are comfortable with your own reasons for wearing a kilt then go for it, but do bear in mind that if the only thing people can remember about you at the end of an evening is that you were in a kilt, then you are definitely doing something wrong.