Clarks are better than sneakers, FWIW.
I also don't recommend wearing a black captoe Oxford shoe with khakis of any color. They're just too formal. Brown derbies are the way to go.
I would also strongly urge you to avoid black khakis. The pant style and fabric are too informal for the color. Also, black cotton pants don't seem to be able to hold their color well, so they look faded after a few washes.
I'm with you. The Napoli seems to be for people with (relatively) large mid-sections but skinny legs. It is the only suit I have ever tried where the jacket had to come in around the waist, and the pants had to be let out. The most generous cut really shouldn't be a drop 7.
Does C&J replace insoles during a recraft? Some makers don't.As for them accepting the shoes, I see no reason why C&J would care if had a topy on the sole. They are going to remove the whole thing anyway.