I shot this gentleman near 57th street the other day and as i reviewed the photo I kept finding all these well done little details that when combined are the secret to the success of his look. 
First of all, I love the aggressive yet subtle (weird way to describe - I know) mix of pattern for his shirt, tie, and suit. This is the type of thing that people who don't understand menswear miss about how a guy can look edgy and completely classic at the same time. I find this level of creativity in mixing patterns and color in every way equal to another slim-cut black Dior Homme suit with a tricked-up white shirt. I'm not saying i don't appreciate Dior but those type of designers don't own the market on true design creativity
He is wearing an Etro suit.Etro is better know for being one of the more colorful and sometimes over-the-top menswear houses ( the Italian Paul Smith) but this photo detail shows they can also deliver high-quality. Notice how the plaid matches at the sleeve seam and how well the plaids match at the breast-pocket.
Maybe Gianni Agnelli was right about wearing his watch on top of his cuff. It is almost unavoidable that your cuff will get caught on your watch which is too bad because he is showing the perfect amount of cuff but the watch is throwing it off balance.
Personally I avoid this by using the clock on my cell phone - sorry watch industry