What's the deal with wearing the shoes of a deceased person? I have heard that Jewish people do not wear them. Why?
The Sefer Chassidim says that one shouldn't wear the shoes of one who has passed away. However, this rule has been interpreted in different ways:
a) Some say that this injunction is based on a Talmudic statement 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.
b) Another reason given is that leather is a conductor of contagious diseases. According to this reasoning, if it is clear that the person did not die from a transmittable ailment – such as if the person dies due to an accident or was killed – there would be no problem with wearing his shoes.
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 were worn by the deceased during the person's final illness.
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, whose death was a result of illness – "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!
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.