I'd do it. I ride a $1200 Specialized Transition Multi-sport. It's a race bike, but it's geared on the slacker end (as far as race bikes are concerned) so that it can also be used as a touring bike (albeit a quick one).
I DID ride kilted a week or so ago... got plenty of looks.

If I do any rides in Maine, methinks I'll do 'em kilted with my riding shorts underneath. That would ROCK. And it'd make great advertisement if I go into business making kilts.