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Il suo sorriso ha sempre un che di malinconico e poetico.

Il suo sorriso ha sempre un che di malinconico e poetico.
His smile always has a certain melancholic and poetic something.
From Lesson 433:Expressing undefinable qualities (un che di)·Italian

Questions & Answers about Il suo sorriso ha sempre un che di malinconico e poetico.

How exactly does the phrase un che di work in this sentence?
The phrase un che di translates literally to "a what of," but it is used as a fixed expression meaning "a certain something" or "an undefinable quality." Here, it attaches to the adjectives malinconico and poetico to express that the smile has a subtle hint of melancholy and poetry that is hard to pin down.
Do the adjectives malinconico and poetico agree with sorriso?
Not directly. While they describe the smile conceptually, grammatically they are modifying the phrase un che. Because un che functions as a masculine singular noun phrase (notice the masculine article un), any adjectives that follow di must also be masculine singular.
Could I say ha un che malinconico without the word di?
No, the preposition di is mandatory in this structure. When you use un che to mean "a certain something," it must be followed by di plus an adjective or a noun to specify what that "something" is.
Since the translation says "His smile", why doesn't the sentence use a specific masculine possessive to match "him"?
In Italian, possessive adjectives like suo agree in gender and number with the thing possessed (il sorriso, which is masculine), not the person who possesses it. Without surrounding context, this sentence could equally mean "Her smile" or even "Its smile".

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