This thread rumbles on, most posts rephrasing what has been said in previous posts.
The cold truth is that few men look good in shorts. Beyond a certain age and weight, most look like dorks: in resorts you'll have herd immunity from critics but in the city you will be judged, like it or not.
If you want the verdict of dork versus classy, ask your significant other. But listen very carefully to nuances in the reply. And don't rely on the opinion of your mum.
Bottom line: If you are unfazed by the judgements of strangers, dress anyway you feel comfortable: shorts, military regalia, tutu or every-day normal. You're on holiday!