this is when I lost it
Warning: Spoiler! (Click to show)
Without the jacket, it could work as a casual outfit, and it might actually work well for some people.
In this case, he comes across as a guy who was wearing a casual outfit, and thought putting a jacket over it would work for the "jacket required" restaurant he was going. It feels like something a teenager would do to rebel against his parents.
Now, I'm not trying to be offensive. I'm just noticing certain parts of his outfit could work, and one piece really wrecks it. Then again, maybe I should cast fewer, or smaller, stones.