Fig.: to be born wealthy; to be very lucky

I wasn't born with a silver spoon in my mouth, and I have to work my buns off to try to make something out of my life

Non sono nato con la camicia e devo farmi un mazzo per cercare di combinare qualcosa di buono nella vita

Of course he is a success: he was born with a silver spoon in his mouth and everything works out well for him

Deve essere proprio nato con la camicia! Tutto quello che fa gli va bene e naturalmente è un uomo di successo

The original meaning of the sentence is "to be born wealthy" and it may come from the ancient custom of wealthy godparents giving a silver spoon - which only rich people could afford - to their godchildren at Christening