That Sanford looks truly gorgeous. Is that really brown? It has a bit of red on my screen. As for the sole, I think getting a the JR double oak sole is an excellent idea. I have a shell penny loafer with a single sole and I'm not a big fan of it. The shell Patriot on the other hand has the double sole- and it has held up excellently. I have done things with this shoe that I shouldn't have done (hiking up a mountain for example) and the sole looks like it has barely worn in.
As for the colour, I think brown on brown looks great.