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a) Some say that this injunction is based on a Talmudic statement2 that a dream wherein a deceased person comes to take away any object is a positive sign—unless the object is shoes. Since dreams are largely a result of one’s thoughts while awake, the fear is that wearing a deceased’s shoes will cause the person to think about it by day—perhaps causing this “bad omen” dream.
According to this line of reasoning, there would be no exceptions to this rule.3
Some say that the rule only applies if the person passed away while wearing the shoes, while others say that they shouldn’t be worn if they worn by the deceased during the person’s final illness
Following this reasoning, some say that the rule only applies if the person passed away while wearing the shoes, while others say that they shouldn’t be worn if they worn by the deceased during the person’s final illness.5
c) Others have a completely different spin on the words of the Sefer Chassidim. They understand the injunction to apply to shoes made of the hide of a deceased animal – “one should not wear the shoes of a dead [animal]”! The reason for this ban is for fear of transmitting the disease which felled the animal to the one wearing the shoes.
According to this interpretation, there is no problem whatsoever with wearing shoes which were worn by a deceased person!6
It would be advisable for you to speak with your rabbi to determine your family/community tradition in this matter. If your community has no defined custom, then you can choose whichever aforementioned opinion suits your taste.
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