(This should not be relied upon for practical halacha. When a question arises a Rabbi should be consulted.)
1. One should cover his head before getting dressed because the head is the most important part of the body and we want to show it the proper respect (Ben Ish Chai Vayishlach 17). Indeed, it is extremely important that all men cover their heads with a yarmulka, or head covering, at all times. This head covering serves as a reminder that Hashem is always above us (See Sefer Umekareiv Biyamin 11).
2. Jewish law requires one to give precedence to his right over his left for all matters. The reason for this is because the right is given greater significance throughout the entire Torah regarding many laws, including the inauguration procedure of the levites in the Beis Hamikdash (the right thumb of the hand and foot were smeared with oil), the metzora purification procedure (the right thumb of the hand and foot were smeared with oil), and regarding the chalitza procedure (the shoe is worn on the right foot) [Shulchan Aruch Harav 2:4].
Therefore, writes the Shulchan Aruch Harav, when putting on shoes one should first place on his right shoe (without tying the laces, as will be explained) and only then wear his left shoe. Similarly, when one places on his shirt and other clothing, such as a jacket or undershirt, he is always to begin with dressing the right arm first and then the left arm. Likewise when placing on one’s pants, socks, and other clothing one first places them on his right leg. In addition, one when is bathing he should wash his right arm before his left. (The head takes precedence before both arms, as noted above.)
3. Based on the above laws, many chassidim have the custom that when buttoning a shirt or jacket they button the right side over the left side, and not vice versa. And therefore take precaution upon ordering a tailored suit and the like that the buttons are placed on the left side and the holes on the right side, and in this way the right side will be worn over the left (See Sefer Ketzos Hashulchan 3:4). The Chazon Ish was also particular that the buttons be placed on the left side and the holes on the right side (as cited in the Sefer Orchos Rabbeinu vol. 1 page 227). The Sefer Taamei Haminhagim (5 in a footnote) writes that the common custom is to place the buttons on the left side, however, on pants the buttons are placed on the right side.
4. Harav Moshe Stern zt”l, the Rav of Debreczin, rules that a left handed person is to give precedence to his right side, just like a right handed person, and therefore should dress his right side of his body before his left. He should also bathe the right side before his left (Shu”t Beer Moshe vol. 2 5:3). Similarly, the Mishnah Berurah (2:6) writes that a left handed person should place his right shoe before his left, just like a right handed person (see also Harav Yaakov Emden’s Sefer Amudei Shamayim seder Levisha 3).
5. As stated above, one places his right shoe on before his left shoe. If one’s shoes have laces then he should put on his right shoe without tying it, and then put on his left shoe. He then ties his left shoe and then his right shoe. When tying shoes we honor the left side because the tefillin are worn on the left arm (Shulchan Aruch 2:4).
6. Harav Shlomo Zalman Auerbach zt”l (oral ruling cited in Shu”t Rivevos Ephraim vol. 4 page 412) and Harav Yosef Shalom Elyashiv zt”l (oral ruling cited in Shu”t Avnei Yashfei 1:1) both feel that since women do not wear tefillin they do not have to be concerned with tying the left shoes first and may put on the right shoe first and tie it (see however Shu”t Rivevos Ephraim 1:5 for a dissenting view).
7. The Sefer Avnei Yashfei (ibid.) writes that a young child should put his shoes on in the same manner as an adult.
8. When removing shoes and other clothing one removes the left item first. This gives honor to the right article of clothing since it remains on the person longer (Shulchan Aruch Harav 2:4).
9. The sages (Gemara Horios 13) revealed to us that there are certain activities that one should avoid since (according to kabbalistic reasons) they are detrimental to one’s memory. According to some authorities performing these actions is biblically prohibited (opinion of Harav Yosef Chaim Sonnenfeld zt”l as cited in Shalmas Chaim 41, see also Teshuvos V’Hanhagos 1:3 and Sefer Shemiras Haguf V’Hanefesh by Rav Yitzchak Lerner shlit”a introduction chapter 18. However, others feel that there is only a rabbinic prohibition – see Sefer Chassidim 1008 [as explained by Harav Ovadia Yosef zt”l in Yabia Omer 2 Y.D. 8] and Sefer Hazikaron by Harav Chaim Kanievsky shlit”a).
9. One of the actions that one should avoid is placing two articles of clothing on at the same time (Magen Avraham 2:3 and Mishnah Berurah 2:2).
10. Many poskim maintain that one may don two shoes at the same time. Therefore, one may don shoes with galoshes (Aruch Hashulchan 2:6, Shulchan Malachim 3, Shu”t Tzitz Eliezer 7:2. See also Maasef Licha Machanos 2:12).
11. According to Harav Shlomo Zalman Auerbach zt”l (Halichos Shlomo vol. 1 page 22) one may remove two articles of clothing at the same time. The prohibition only extended to donning clothing, not removing them. However, Harav Yitzchak Eisik Yehuda Yechiel Safrin zt”l of Komarno, known as the Komarno Rebbe, writes (Shulchan Hatahor 2) that removing two articles of clothing at the same time is also detrimental to one’s memory.
12. It seems that women are not restricted by the above laws and they may don and remove two articles of clothing at the same time (since according to many poskim women are permitted to perform actions that cause forgetfulness- see Mishmeres Shalom 72:2, Sefer Hazikaron chapter 2, Shu”t Yad Yitzchak vol. 2 84:17).
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