Dylan,
I had the opposite bias when I was first considering a kilt. I didn't want to look too 'loud', and I didn't want to look like I was dressing up. I live in Edmonton - by reputation, a much less 'hip' city than Calgary [but privately I'd debate you over that]- and the very first kilt I wore was solid black. No leather, no metal, nothing 'butched up' about it.
The only comments I got on that first day were all positive and all called it a kilt.

After that, I made myself a tartan kilt and have had people call it a skirt on a few occasions. I find after talking to these people, however, that they [almost] all knew it was a kilt, but were trying to get a rise out of me.

Now, if you were to go with a kilt like Steve makes at FreedomKilts, or like the UK, or a Pittsburgh Kilt, then you have even less to worry about than I did. These are all strongly masculine garments, both in cut and in material, and the only women I could imagine in them would be military women.

Derek

PS: Except for the kilt I've got on order from FreedomKilts, I'm a total tartan convert now. I love the look of a striking tartan [especially one you can talk about the history of].