Joe
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This looks like the 1940's to me. Florida Street. And the people seem as prosperous (or more so) compared to the US and Europe at that time.
In the Pizza Poll thread is a photo of a pizza joint in Boca - and all the men are wearing suits.
In old pictures of Cuba the contrast is even more pronounced with old photos of people dressed in suits where in the same square today people are wearing old shorts and t-shirts ready for the rag pile.
Here in Sevilla, people dress up on Sunday and promenade just like the photo - except not as fancy!