Hi. I am a student in Calgary. I am not completely new to kilts, having wandered into them through my association with Living History (specifically the SCA, where they are quite popular).
When I am at those events I can get away with a ladies kilt that I hemmed and moved the buckles on (no one ever seemed to notice it fastened on the wrong side) or a literal true belted plaid.
I never really felt comfortable wearing them outside this safe enviroment (more due to being embarassed by the quality than anything else) and I finally have a little money and am about to order my first "real" one for casual wear. I am thinking about ordering a stillwater, but they are a bit long. I would like a bear, but that will be my next one since I don't want to wait that long, and a stillwater will still be cheaper even with the exchange.