In truth, it seems to me that the first, and most difficult, hurdle to overcome would be being an accomplished tailor. The second would be how to make a proper kilt (not that this is a small hurdle, but I think it would be a more surmountable one if you already knew how to sew box pleats down from making dresses).

If I was a DIYer, I could learn everything about making a kilt, but the fact is most anything I made would look like someone vomited tartan onto me. I'm just not handy with a needle and thread. However, a skilled tailor could learn to make a new style of garment (at least more easily than I could learn to make anything).

I think you're right about the cost, though. For a tank you would have to either provide your own cloth, or have the tailor buy special for you. It might not be a bad idea for a pinstripe kilt suit or a PC, though.

It could be a win or fail, but I would only attempt it with a tailor who has proven to be good.