Can a Jewish person wear a picture of a skull on a garment or on a piece of jewelry?
Shalom, From a purely halachic perspective, I do not know of any prohibition against wearing a picture of a skull. Skull pictures (as far as my limited knowledge goes) are not related to any form of idol worship, nor do they have any licentious references. Nonetheless, wearing of such items is certainly not in line with modest Jewish behaviour. To try and imitate pirates - unscrupulous souls who made their living by theft and murder - is not appropriate. Also to wear clothing that marks one out as associating with the undesirable elements of society is inappropriate. So if the question is whether there is a halachic source to wear such an item for a specific need (as in a play etc), then it is permitted. But if one desires to dress in a modest and correct fashion - skulls are "out". Blessings, D. Sperling.