My Scottish uncle was a singer/actor who would dress in full working-class-Sunday-best tartan to perform Burns' Suppers etc. One day about 20 years ago. while we were visiting, and walking through Glasgow, a bunch of pre-teen boys who were on the other side of a chain-link fence started taunting my uncle (he was suited up for a performance he did in a park):
"Oy! Are ye a Trrroo Scotsman?" "Have ye got a wee black dog too?" "Are ye wearing any knickers [underwear]?" "There's an Englishman he's trrrryin' tae kill ye!" "Och Aye! He's a trrroo Scotsman!"
It was so weird to hear these very Scottish boys mock the most prevalent icon of being Scottish. This is when it hit me: men DON'T wear kilts in Scotland, unless it is Sunday, or a wedding, or if they are in a Scottish regiment. In Scotland, men wear black cotton twill trousers. I have seen more people "walking around in kilts" here in the US then I have seen doing so in Scotland (stands to reason, since I don't actually live there).
Tha' doesnae answer the question, but. Would I wear a kilt? At a wedding, perhaps, if someone sprang for the $1000 for a decent getup. Cheap kilts look like skirts.