Dorme con addosso le scarpe.

English Translation

He sleeps with his shoes on.

More and more I come across sentences where I can easily solve the cloze but which I do not understand at all when I start thinking about it.

This is from the preposition section.
However, “addosso” is not used like a preposition here. It is more like an adjective.
And furthermore, the word order sound strange to me: “… con le scarpe addosso”?

Obviously, ou can do something like that in English.
In German it would be a gross mistake.
“He has shoes on”
= Er hat Schuhe an. (verb = anhaben)
“He sleeps with his shoes on”
Er schläft mit angezogenen Schuhen. (You need a real adjective here.)
In Italian that would be like “Dorme con le scarpe indossate.”

So my questions are:
Can you do something like that in Italian or is it an all too literal translation from English?
If yes, is the word order correct?

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con addosso is an idiomatic colocation in Italian and simply means wearing.

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