When walking around Milan, you see a lot of very dark suits and black shoes. It may be the younger fashionistas in RTW but it looks good.
I have heard this a couple of times lately, black shoes. Which is odd seeing as I understood black to be anathema to the Italians. I clearly prefer brown shoes and have been on a 5 year tear purchasing them in different shades, styles. Perhaps it's the slim, no break trousers that make them look sharp instead of conservative.
I rarely see a break that is neat and intended as opposed to just slobbery, and the ones above are the latter. There's a misconception that one needs the ankle-flashing Pitti capris to get straight-hanging, breakless trousers... a good tailor can interface the bottom of the trousers to give a clean or slight break pending on preference.