UC, that's a perfect fall outfit, which suggests that I should be jealous of your weather right now.
Engi, I wish you'd gone for different shoes. A lighter color (deep tan) and more casual style (full brogue or loafer) might do you some good. I'm normally not crazy about chiseled lasts, but I think a slightly sharper edge there could look really good. I feel like the shoes, while elegant, are conservative enough to appear a little staid compared to the rest of your rig. You could also go the other way -- longwing gunboats might be cool with a rig like this.
Don Cologne, I happen to like the shoes, and though I agree that you might be well-suited aesthetically by a less built-up shoulder, if you prefer/are more comfortable in this kind of cut, then you're better off with it. You shoulders might also be square enough that they'll have a relatively constructed shape even with less padding/stiffness.