Antonio, I think what you are doing is fantastic! I love the look with the navy short sleeve shirt and gray trousers with side tabs...great!
BTW, I've tried Isaia in a 36r and found it a bit full which was very surprising. In general, how will Eidos be cut in comparison?
Lastly, your formal jacket reminds me of something Lapo Elkan might pull off quite nicely. And in the right setting, I would give it a shot myself !