I'm in Lakeview in the South West.

I don't wear mine on a daily basis, either, but sometimes I'm just in the mood, so I put it on. I've gone down to Chinook Center with it on one time when I went down there with a friend, and it wasn't really an issue, but I did have a funny encounter at a cookie place, where the young worker there asked "What's the ocassion?", and I played entirely dumb replying with "... for what?", to which she replied with "Well, for wearing the kilt!" and I told her that "I don't need an ocassion to wear a kilt!" and walked out

That's about the most negative comment I've gotten, and it wasn't even entirely negative. With all the Scottish heritage in Calgary, I doubt you'd run into any problems.