Dress Shoes for Metatarsal Support (also: how do these look?)

[jrbrown1991]

First: can you recommend any dress shoes that would be good for metatarsal pain? Basically, I need a *very* stiff sole, whose stiffness extends up to (but not including) the toes. Maybe 3/4 shank? Also, I use orthotics and my arch is too far back. So, if the shoe becomes narrow at the arch, my orthotic won't fit; it'll ride on the side of the shoe.

Second: see the attached images. How bad are my boots for my outfit? I could probably dye them black, but obviously I can't change the shape or size.