I think for me it took about 2 hours. I bought my first kilt about August of last year, a Blackwatch phillabeg at the MD Ren Faire from Wolfstone Kilt Company. They were kind enough to let me leave my jeans there and told me to go out and enjoy myself. By the end of the day I had returned to their shop, purchased a Royal Stewart Ancient, placed an order for a third one in County Monaghan tartan and have been quite happy with wearing kilts since. I must confess one thing, I'm sorry that I didn't try one on sooner (like about 20 years sooner) I now wear them when I feel like and wearing one to work is no problem, the ladies in my section love it (I'm the only guy in my section, the rest plus the boss are all ladies) and my boss has no problem at all. The soldiers just look at me and grin, and every now and then I get a whistle from one of the female troops that come through my section. As for getting strange looks, I'm used to it, I have worn my Confederate Officers uniform in to work, (my wife and I are both Civil War Reenactors) I get more questions from that than when I wear a kilt in to work.

Brian