I would really look into one of those walking jackets for him. If that doesn't work I don't know of anything else.

On a sidenote, growing up we had a cat that would sit on the curb and watch both ways. If he seen a car at the corner on the other side of the road or a car getting ready to turn he would sit and wait. When it was all clear all ways then he would run across. We had to sadly put him to sleep after he started attacking my mom and me.