As a couple of others have already stated I mostly wear the kilt for special events and evenings out. I will wear my kilt at other times also, but by no means on a daily basis. I used to have to wear a coat and tie daily when I was a banker, and believe me on sunday, or an evening out on the town it was the last thing that I wanted to wear.

You said that you have several UK kilts and a generic model. Have you thought of investing in a hand-sewn tank in tartan? It might be just the kickstart you need to see the kilt as a special garment and not as something that you feel you must wear. As another said if you do go with a traditional tartan be sure to wear sporran, flashes, belt, i.e. the whole nine yards. It will definately put a different perspective on kilt wearing.

Wear the kilt when it feels comfortable and wear pants (it's ok to say the word) when they are appropriate for the activity. Remember that variety is the spice of life.