Rei

I think there are a lot of guys exploring a similar look. Myself included. Regular fit works well for shoes. You can certainly wear boots underneath regular fit jeans, but you won't like the look of the boot over them. This is where skinny jeans are great. They have a nice line continuing into the boot shaft. Note: You will probably have to have the boot shafts altered to fit. Ladies boots tend to have more meat in the calves for a given size than we guys have.