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It is possible. But it is good at the sole condition that you genuinely don't care (i.e. you're not worried enough to ask this on a message board).
NoBasically this is what I tried on at the store (was already wearing polo/shorts/shoes).
Sprezzatura.I would say a lot of the time people that look like they don't care, and look good, actually do care. It can take a lot of effort to make things appear effortless.
No
Polo, shorts, sockless boat shoes with a F/W jacket like that? On another note, the jacket looks awfully short.
If you are going to a board meeting at the yacht club then it is appropriate wear. Otherwise it just makes you look like a retro yuppy tool.
Sprezzatura.
As for the question, I think it's becoming somewhat of a trend to use shorts with a blazer (or then It's just here in Finland). I think it can look very fresh, but most of the time it looks rather sloppy and just plain dreadful. I wouldn't go for the look, but I know many that would. As long as you look confident, you can pull something like this off (like someone already mentioned).
Blazer + shorts = prep classic. Still common in parts, especially among the college set. But like Nantucket reds and other context-contingent clothes often misused on the forums, it's the type of thing that works in a particular setting. If you're the only one sporting the look (and particularly if you adopted it after seeing it online/in a magazine), tread cautiously.