Actually, if this can be of any reassurance, I buy from the States all the time. I tend ti buy smaller things because every single time I'm hit by customs.
However, if you ship via an insured and trackable posting method you should be safe.
The list of prohibited items posted on the USPS is, from my direct experience, terribly out-of-date. I have received loads of leather products from the US and the only thing that might be asked to the recipient is a certification that the leather does not come from endangered species. So if the good you have to ship is calf, goat, or other "normal" leathers, no problems at all.
The main concerns regarding posting things to Italy are these:
- Make sure to describe correctly the content of the package. Do not omit anything contained in it. I had a parcel bounced back to the sender because it contained several stuff and only part of it was listed on the customs declaration. So go ahead and be very specific about the parcel: "Used leather bag" or similar descriptions are ok; I would also omit to specify the brand of the bag because yes, *some* customs offices in Italy are a bit shady.
- Make sure the buyer knows that you will insure the parcel with its full value and that he/she will end un paying customs duties on it. As a personal favor, you could mark the parcel as a gift, so that the buyer will end up paying only import duties but not VAT, but that's up to you. I know this is a hot issue because everybody appreciates when they get a parcel without having to pay customs duties (this is discussed a lot in every area of this forum) but many sellers do not want to do this. Just *make it very clear to the buyer* that you are not responsible of customs. In Italy you must pay a percentage for anything over 45 Euro (50US$).
- If possible, avoid completely the postal system. If the buyer really wants the item, he/she could agree to use a courier instead of the post. It will cost more, but it is much safer that the normal post.
- If you still send by post, expect that the delivery times are twice those stated by the USPS itself. So if it's 5-7 days expect two weeks, etc.
- I have to say that *eventually* I always get all my parcels from the US, it's just a question of patience!