The Bermuda guys look a hell of a lot better to me than the man in the OP. Not sure my bony knees would allow me to pull it off, but at least there's some tradition to it, Lebron and Bruno Mars notwithstanding.
The Bermuda shorts with jacket look always reminded me of school uniforms. Back when boys wore blazers and short pants. And I suppose that's where the tradition originated. It's a very "boyish" look. The picture the OP posted is as far removed from that tradition as you can get.
Side rant: I can't stand auto-correct and predictive text. Why in the world would my tablet make me type "shorticulture"??