Seeing as AA has yet to clarify what he means, I'll take a crack at it. Could it mean wearing a kilt in a way that is traditional, but also classic, current, and up to date?
I'm really hoping auld argonian will clarify his statement, because I took it to be completely different than you did. I interpret his response as meaning he wears whatever he would normally wear in everyday life... but with a kilt. This might mean wearing modern shirts (say, a polo style shirt), etc.