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Answer:
The Church doesn’t have a specific official position on this matter, but we can apply some good Catholic moral principles to arrive at a well-founded conclusion.
What is the purpose of the jewelry? Sometimes you will see skulls on tombstones, even skulls with crossbones, as I’ve seen in Boston cemeteries. Some also had worms coming out of the empty eye sockets. Though jarring, this tombstone art is intended to help people realize their mortality and thus live their lives well and plan for death accordingly.
On the hand, other skull jewelry can be used to frighten and intimidate, as is sometimes seen with the ornamentation of some motorcyclists, whether on their persons or their bikes.
Thus, the question you should ask is: what message does the jewelry I’m considering wearing convey, and how will it likely be perceived by the average person? If you can’t answer these questions positively, I would recommend instead wearing jewelry with a death theme but which conveys messages of merciful love, triumph, and hope. That is, par excellence, a crucifix.