Q. Is it true that one should not wear the shoes of dead people?
A. First a general comment. Rabbi Akiva used to say, “Let not your foot be without shoes” (Pes. 112a). A Torah scholar should not go barefooted or with patched shoes, and even an ordinary person is advised not to go without shoes even in the privacy of their home. Shoes are so important for one’s dignity and comfort that the Talmud says, “Sell all you possess in order to buy shoes” (Shab. 129a).
Your shoes get so used to your feet that they become an individual part of who you are. Hence it became customary in some places not to wear a dead person’s shoes, presumably because the shoes were an indication of that person’s identity. However, Rabbi Yehudah HeChassid, author of the medieval pietistic work, Sefer Chassidim, prohibited only the shoes worn at the time of the person’s death.