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I would say that the second gentleman carries it off much better than the first. As someone else pointed out, nicer shoes would have made a huge difference, a nicer shirt wouldn't have gone amiss either. Overall, first person - nothing special, second person - nice outfit.
I think the contrast between the two outfits is interesting. The second photo shows a pretty standard outfit, but the first photo is a bit different.
Unless it's just the photo or the angle, the guy in the first photo has more closely fitted clothing. Slimmer jacket, almost a jeans cut in the pants. I think it looks kind of cool, but doesn't it violate the general warning against wearing casual clothing too tight?
It is the California tux. It's not intrinsically a bad look, as we can see here (though I think these are still boring in a bad way and hardly creative interpreations). But it's the iterations of the look worn to more formal occasions, with metal buttons and horrible shoes, and ill-fitted in every way, that give it the poor reputation it may or may not deserve.
I like the first guy better. The fits and cuts are nicer. The second looks a bit sloppy and self-conscious.
BTW, there is no rule that says casual clothing must be loose. Moleskins and cords are traditionally cut slimmer than normal suit trousers, for example.