To me, it seems like there's a false dichotomy. Happiness vs. appropriateness. Has the gentleman in the photo somehow convinced himself that the only watch that could make him happy is one completely opposite the style of his tuxedo?
Is someone else only able to feel happy with a dress watch, even when wearing shorts and sandals?
I own watches that make me happy. I'll wear a dressier one with a dressier outfit, and a more casual one with a more casual outfit. I'm happy when each gets some time on my wrist.
There's a reason to avoid a … style mismatch, like the one portrayed above. Judging someone by their watch (or other article of clothing, or their entire outfit) is superficial. But this world is full of superficial people … so the superficial details end up mattering to them. If they can be so easily swayed in my favor, why not make the trivial level of effort to shape their opinion of me?
Clothing (and accessories) are a form of communication. Like all communication, it can work for you, or it can work against you. There is a possibility that that choice of watch is conveying the precise message that gentleman (in the original photo) wanted to send. Or it's possible that he does not know what message he's sending out there.
But I can say with 100% certainty, the message that he's sending is not one that I would want to make.