Motorcycling while wearing a kilt is the same as motorcycling while wearing any other style of clothing. The only thing I do differently is tuck the ends of the pleats under my thighs to prevent the hems from resting on the hot exhausts and to keep the general public from an unobstructed view of ...
As for what it looks like, I don't give flyin' ???k. Really, it's my own business about what might be looking good, bad, right or wong as I ride. Look and see, we'll find that in days of yore those kilted on horseback also had windchill and bouncing hems because of galloping horse. I live in Seattle, and find it thrilling and occassionally chilling on the hills of the city as I motor about. The people here are quite friendly also. Many complimentary comments are given to me as I go here and thereabouts!
Anyway, I ride my MC daily, and more frequently in kilt because it's simply convenient to mount and ride. I also don't want to put on the trousers for a hop the grocer. Naturally, I most often don my chaps against the windchill or for longer distances. However, clothing is clothing, so no problem for me when it comes to being a man wearing a kilt while riding his MC!
I guess people will eventually become more accustomed to seeing man on a motorcycle with kilt flapping in the whip of the wind!