In many communities, there is a Minhag of doing Kapparot in the eve of Yom Kippur, what is the best way to do the Kapparot, with chicken or with money for charity?
First of all, we need to clarify that there is no Mitsva in the Tora to perform the Kapparot or any kind of animal sacriﬁce in the eve of Yom Kippur. In our days, as Maimonides explains "en sham el-la teshuba", there is nothing else but Teshuba to atone for our sins. Teshuba is a serious mental and emotional process of retrospection, which leads to admission and confession of our flaws and bad habits, and which ultimately will lead us to resolve improving our behavior .
Kapparot is a practice which was initiated by the common people -not by the rabbis- that apparently started at the time of the Geonim (year 800-1000 CE). The Kappara made with a live animal suppose to help inspiring our Teshuba. By seeing the Shehita (slaughtering) of the chicken, we realize the extreme fragility of our lives. We then reﬂect on the appropriateness of doing Teshuba while we are alive. This is, by the way, the frequent explanation for the effect that the qorban - in the times of the Bet haMiqdash- had in the sinner's consciousness.
However, soon after the custom of Kapparot became more popular some prominent Rabbis like Ramban (Nahmanides) raised their voices against this practice. Maran Rabbi Yosef Caro (1488-1575) the author of the Shulhan Arukh -the supreme Code of Law for Sephardic Jews- explicitly and in very harsh terms disapproved the practice of Kapparot with chicken in the eve of Yom Kippur. Moreover, in the first edition of the shulhan 'arukh, Venice 1565 it is written by Rabbi Yosef Caro in the title of siman 605, where he talks about Kapparot מנהג כפרות בערב יום כפור מנהג של שטות הוא. "The custom of Kapparot in the eve of Yom Kippur is a foolish custom". In later editions the editors cut the las line. (see the source here)
Why such opposition to the Kapparot with chicken?
First, as Nahmanides said: mishum darke haemori "because it is similar to the practice of idol worshipers" . (Even today, many cults like Macomb, Vodoo, etc use a small chicken as a sacrifice to be given to their deities.You can Google for example Eshu or Elleggua a major idol-warrior of Santeria which must be worship by sacrificing to it a small chicken).
Second, the argument that the Kappara performance looks like the Korbanot performance, made the rabbis very concerned: because slaughtering an animal as a sacrifice outside the Bet haMiqdash (haqrabat hutz) is considered a serious Biblical transgression . For this reason many rabbis in the past asked to forbid the consumption of the chicken that was slaughter in the fashion (or intention) of a qorban. The Rishba, while still opposed to the Kapparot with chicken, allowed to eat that chicken (which was usually given to the poor) because it is not one of the animals who were offered as a sacrifice in the Bet haMiqdash.
Third, since so many people want to do Kapparot on the eve of Yom Kippur, the Shehita might not be done with enough care and attention in terms of the checking of the the knives and other ritual details. This is the point brought by Rabbi Obadia Yosef (who in the past supported the Kapparot) to favor the performance of Kapparot with Tsedaqa (see this).
There is yet another problem, which should be of a great concern when thinking about doing chicken Kapparot. Because of the great demand and the short time to slaughter so many animals, the chicken are too often mistreated in the process, left for days in cages without food or water. This is a serious transgression of an explicit Biblical prohibitions instructing us to treat animals with respect and avoid unnecessary suffering (tsa'ar ba'ale hayim). The new Ashkenazi Chief rabbi of Israel, Rabbi David Lau addressed this issue last Sunday (see here).
Lastly, if the person who does the Kappara would actually eat the chicken or would give directly the slaughtered chicken to a poor person, then we could view this Kappara as a form of Tsedaqa. But people who do this type of Kapparot would very often take seriously the wrong idea of a transference of his or her sins into the chicken and therefore they would not conceive eating those chicken "full of sins". And not all chicken get to the poor, many times for this same reasoning. The truth is that many of these chicken are not eaten but just wasted. And if one kills an animal unnecessarily, one transgresses another explicit Biblical prohibitions bal tashchit, i.e., unnecessary waste of the resources that God granted us.
In conclusion, the best way of doing Kapparot is by giving Tsedaqa (=charity for needy people). In this case, none of the above mentioned problems would apply, and in addition before Yom Kippur begins you will be fulfilling the beautiful Biblical commandment of charity. Which is a Mitsva with no negative side effects and which brings a great zekhut (merit) to the giver and great relief to the recipient וצדקה תציל ממות
Rabbi Shelomo Aviner explains the different ways to do Kapparot
Wearing leather shoes on Yom Kippur - is it a Minhag or a strict Jewish law?
Wearing leather shoes on Yom Kippur is one of the 5 prohibitions of the day. The Torah did not command us to be barefoot but rather to avoid wearing shoes that are made of leather. Other type of non-leather footwear is permitted. This restriction applies just to leather shoes--which is a "dress" footwear--and not to other leather articles, such as a belt, a leather Kippa, etc. This prohibition is called in Hebrew ne'ilat hasandal and it applies for men and women. Moreover, unlike other Yom Kippur's prohibitions, such as fasting, the prohibition of wearing leather shoes should be taught to children as well, even when they are still not at the age of fasting.