I haven't worn one for about ten years.
The kilt question is a bit of a tricky one for me. It very much depends on the occasion. The thing is that there is a tendency in many cases for kilts to be worn by people who are not Scottish but want to pretend that they are. Most people I have known who wear a kilt outside of very formal occasions like weddings or funerals speak with a posh English accent.
So, I wouldn't generally wear one for patriotic reasons, because it would make me feel like I was one of these wannabe Scots.
In any case, as far as I understand, the kilt (along with most tartans) is a Victorian invention, promoted by large landowners who liked the staff working on their estates to look picturesque. Prior to that, they were not commonly worn, unless you go back to before the battle of Culloden in 1746 (after which the wearing of tartan was banned by the English oppressors) in which case people wore what was known as a plaid, which was a large length of cloth that kind of went over the shoulder and covered the whole body.
In any case, before then it was really a Highland form of dress rather than a "Scottish" one.
So in essence, wearing a modern kilt denotes submission to the landowning classes and as such I would be disappointed to see any U75 class warrior wearing one.