I don't see a city/country problem there, CD, though "city/country" is kind of not doing it for me anymore as a major paradigm. It's part of it, but it ain't the be-all-end-all.
I do think those trousers are a shade too dark. A gray in the same shade as the green in the coat would probably sing, or light tan moleskins. Square/tie/shirt/jacket is great -- unistripe oxford, perhaps? The jacket is very Vox.
As for stitches' rig with the blue trousers, they work well, but there's a lot of blue all up in there. Pink shirt? Pink shirt. Tie with some pattern? YYY-yep.
EDIT: Wrote that before your whole post there, stitches. I don't think the "optimal choice" is always the thing to do. I'm never in a suit, for example, but if I were, I would probably go for the path of least resistance. Similarly, if somebody only occasionally wears a sport coat, then it makes sense for them to do things that are absolutely going to work -- always the "optimal choice."
If you wear the same type of thing a lot, then making the safest choice everytime could easily seem boring. I'm in that camp, but I can understand why some folks might not feel that way.