It sounds like you’re planning to wear shorts in town (you mention “the street”) as well as in the evening. Many on this forum will disapprove on general principle, although we appear to be a diminishing cohort.
The principle, specifically, is a belief that shorts make men look like boys and thus are only appropriate in outdoor, recreational environments like the beach or the mountains where men can be expected to act, and look, like their inner lad. Even there, not after dark.
Beyond that is a more practical problem with wearing shorts in town, which you have in fact identified—namely the problem of footwear. As noted by others, the best shoes with shorts are espadrilles, huaraches and other such casual, closed-toe footwear originating in tropical climes. But they are unsuited for padding about on pavements all day, or night.
The solution is not to wear shorts in town.
I realize you probably don’t want to hear that, but the fact is that legs don’t actually perspire all that much. (As proof, consider that men who wouldn’t think of wearing the same shirt two days in a row in summer will regularly wear trousers over multiple days.)
Is your town such a living hell that wearing slacks while darting from one air-conditioned building to another is untenable? If so, and if loafers aren’t your thing, you must resign yourself to sneakers
