When I first read the topic heading, I was ready to cringe, but this guy seems to make it work and all the elements work well and work off of each other in an interesting way. I certainly couldn't pull it off, but I give credit to the guy for being able to do so.
The shades make it work. He'd look about half as good if he didn't have them.
Definitely agree that the shades are key, but I think that the coat is a great touch as well. The whole look just hangs together nicely.
What's interesting (at least to me) is imagining the same guy in a different haircut/style. The outfit really gives him a lot - his face is not that unusual/striking. With a Trad haircut and outfit he could be an investment banker.