Cowboy boots seem like a bad idea because they are slick on the bottom, if you look at all the HD road gear boots, none of them are cowboy boots. I just stick with my HD boots I bought, thick soles,lugs for traction, and they have the HD emblem on the side, which is cool. I would only wear ostrich skin boots if I was out and about with the wife (dinner, shopping, etc.) so she wouldn't get offended if I didn't wear them riding. Just my opinion.

 

I ride with cowboy boots all the time. I have a pair of Ostrich as well. Very comfy but make sure you walk around on concrete for a while in order to scuff up the soles so they grip better.