You are probpaly right about my first pass at a heel. One of my friends told me the same thing. Get him in a shoe he thinks he cold wear then walk him into the ground. I am doing some more resarch and will put up my finds. Yes, I think its better not to get into a discussion of the prizes in public.
Here is a shoe that comes in wide and would appear to have plenty of toe room. The heel is only 3 1/4" but that ought to be enough to give him the feel of heels. By the end of the day those straps on top will have taken their toll. I think I will give him some moleskin and tell him he might want to take it along. I am thinking we ought to be wearing the same shoe to be fair. Red for me black patent for him?
Here is a flat that comes in W. I decided to get white so as to avoid an argument over the color.