With the other one do you mean Cerruti or Angelico?
I can see people seeing the Cerruti as a bit too boring, but IMHO it's a perfect Fall jacket. Pattern matching and fabric are awesome, and at that price it was really a no brainer.
On the other hand the Angelico one is a bit "crazier", great for the aperitivo, but definitely less versatile. Due to a lower discount, price is similar, but quality is slightly worse.
The Angelico. I can't even see it working in Milan, personally.