Okay, I'm a sixth-generation Texan, and unless I'm wearing shorts and flip-flops, I'm wearing boots and jeans.

I've seen several wearing cowboy boots and hats with kilts (and yes, even with a PC) at the various Highland games we attend around Texas, but I've got to say that I don't care for the look, and don't think it works. Personally, I think it looks a bit silly and costume-y (if that's a word).

IMHO, better to choose one look or the other, and if you choose to wear the kilt, then leave the cowboy boots at home on the day you attend the games.

For what it's worth, I regularly see one tall, older gentleman at the various games who's always sporting battered boots, well-worn Wranglers, an old Stetson, and a well-cut vest in his clan tartan. I think that's a far better look if you want to go Western.