Ran across an article on eHow titled How to Bike in a Kilt. That is about the last topic I would expect to find on this site. Looking over eHow there are articles on wearing the kilt in general but specific to riding a bike surprised me. The article is written by a lady. I don't know if she intended this for ladies in kilts or men. When I see the word "kilt" to me that is a man's garment so I read this from a man's garment perspective. The reason I ask is she comments on the length of kilt from long to short. She also did not say if she had experience herself riding a bike in a skirt. She does not state the type of bike but I would have to say she assumed a standard road bike. On a road bike you are basically in a vertical position if you have the seat high. Wearing a standard length kilt the center bar would get in the way unless you have ladies bike. For men in kilts I would assume most would have a standard bike with the bar. This bar may actually help to keep the kilt in place as you ride. Getting on and off the bike presents possible exposure situations as she states. Wearing something under the kilt is a must for two reasons. First is exposure which you don't want and the second is problems with chafing.
As a bike rider myself I have tried to ride one in a kilt. My bike is a recumbent which has the rider in a more horizontal position. I have made two attempts at riding with a kilt. The kilt happened to be a standard Utilikilt. The standard kilt does not have the modesty strap as you will find on the Workman so that was not an option to try. I wore something under it for reasons stated above. With my legs out in a horizontal position the wind would push the kilt back. At no time did the wind attempt to flip the kilt up it just pushed it back. I had no idea what was showing under the kilt for those approaching me but there was a lot of leg showing if nothing else. I found myself fighting the kilt material trying to push it back. I quickly determined that this was making for a rather uncomfortable ride. Even with something worn under the kilt I suspect those approaching me would not appreciate the view even if there was nothing illegal about it. I made both rides on a side street so I could test the concept without any riders or walkers present. On a regular road bike I think I could have gotten away with wearing a kilt but not on the recumbent. If the kilt was modified to add a snap or something to connect the back with the front between the legs it may work. This is probably not worth the hassle. So it looks like my bike riding this season will be back in shorts.