There are indeed some lovely bikes shown in this thread. I do remember we did have a thread a number of years back showing our rides.
The RAT pack (Triumph riders) wear their kilts to RTE events. I have a few customers in that group.
I must say riding a cruiser kilted is a challenge, I found it easier on a sport bike or sport tourer as it is easier to tuck and pinch. The forward leaning position also helps.
In the colder weather I rely on a heated vest, and heated grips. MY ST1100 provides some weather protection as well, so it isn't too bad out there for me.
In the early years of Utilikilt they had photos of the workman's kilt and the model was wearing waffle long johns. That is an option I guess to ride kilted and not worry too much about the kilt flappin in the wind.... reminds me of a song "dust in the wind" change the lyrics to "Kilt's in the wind" ;)