It takes a bold man with little fashion-fear to wear this outfit, and yet, despite being risky, it is quite understated and essentially just a twist on the conventional smart casual look.
The way David has accomplished this is by wearing the more quirky elements on the bottom half — grey harem pants and silver shoes — and then keeping the top half modern but more traditional so it takes a second glance to get that it is not what you were expecting. Also, by working all the elements in tones of grey, the composition is very cohesive and gentle. I would have liked to have seen a pocket square in the jacket just to lift it a bit and play up the irony.