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[According to Kabala] one is to be careful not to put on two pieces of clothing together, as doing so brings one to forgetfulness. [Thus for example if one’s shirt is inside his coat, or his undergarment is inside his pants, he should not wear them together.]
Removing two pieces of clothing together:
Some Poskim rule it is not necessary to beware against removing two pieces of clothing together and the above adherence is limited only to wearing them together. However others record the above adherence equally regarding removing the clothing, and so writes the Mittler Rebbe that “It is a known fact that the removal of two pieces of clothing together brings one to forgetfulness”.
Practically, those who are meticulous are also careful not to remove two pieces of clothing together.
*Based on the above all the adherences brought in the Q&A below apply likewise when removing the clothing .
If ones hat fell off together with his Yarmulke may he place the hat back on his head together with the Yarmulke?
Based on the above ruling one is to beware not to place his hat and Yarmulke on his head simultaneously. The same applies regarding one who wears two Yarmulkes, one under the other, that they are not to be placed on the head together.
May one place a plastic rain cover over his hat and then wear the hat?
Some write that doing so is not problematic being that the rain cover is not considered clothing and is simply there to protect the hat.
May one wear two socks, one within the other, at the same time?
If ones shoes are inside his rain boots may he place them on together?
If ones Tallis slipped from one’s head together with his Yarmulke is one to avoid placing it back on his head together?
Some Poskim write there is no need to avoid doing so being that the Yarmulke is nullified to the Tallis.
May one lift up or lift down two pieces of clothing together if he is not removing it from his body?
- Example: When placing on Tefillin may one roll up two sleeves together and then place them back down together? When using the bathroom may one remove his garments and then replace them together?
Some write that one may wear and remove them together as the above adherence is only applicable when completely removing or wearing clothing from or to one’s body.
Sparks of Kabala:
The reason that placing two clothing simultaneously causes forgetfulness is because every piece of clothing is an Or Makif and one must have space between the two pieces of clothing in order to allow the Or Makif to enter and encompass the entire clothing, hence banishing all Kelipos. One who wears two clothing simultaneously prevents the Or Makif from entering between the clothing which allows the Kelipos to remain in that area. It is these Kelipos that are responsible for forgetfulness.
Having another person hand one his clothing?
Many are careful to follow the Talmudic warning not to have another person hand them clothing in the morning [prior to prayer]. They rather take the clothing themselves. Nevertheless some are lenient to allow the other person to bring one the clothing, and then put it down, thus avoiding taking the clothing directly from his hand. One may certainly be lenient in a time of need.
 Kama 2/3; Basra 2/3; M”A 2/3; Arizal Shaar Hakavanos
 Basra 2/3, Based on Arizal Shaar Hakavanos Inyan Birchas Hashachar
 Basra ibid; However in Kama ibid the wording is “It is good to be careful”
 To note that in Kama ibid Admur adds the word “together simultaneously” while in Basra he just writes together.
 The above adherence is only written with regards to wearing two pieces of clothing together. No mention is made in the Poskim or Mekuballim regarding whether this law applies when removing the clothing; if one may remove two pieces of clothing together. The following is the available resources on the subject.
 Orchos Chaim [R. Gedaliah Lipshitz, brought in Shulchan Melachim on the Kitzur Shulchan Aruch]; Halichos Shlomo 2/22
 Shulchan Hatahor 2/1 [Komrono]; Minchas Aron 22/12; Yayin Tov 11; Shraga Hameir 4/87
 Ateres Rosh Shaar Yom Hakippurim 2 [p. 29]
 See Kovetz Yagdil Torah (Israel) vol. 1 page 122.
 Ruach Chaim 2/3; Kaf Hachaim 2/6
 Piskeiy Teshuvos 2 footnote 13; However Tzaruch Iyun from the law on Shabbos in which many Poskim rule it is permitted to wear this cover over one’s hat on Shabbos even in an area without an Eiruv being that it is considered like a clothing. [See Minchas Yitzchak 3/26; Sheivet Halevy 1/61; Rashdam 4; Chelkas Yaakov 2/6]
 Yifei Laleiv 2/3
 Aruch Hashulchan 2/6; Pnei Meivin 226; Shulchan Melachim 3/17; Tzitz Eliezer 7/2
 Miaseif Lechol Hamachanos 1/12 based on numerous Poskim that consider shoes to be clothing
 Ashel Avraham Butchach 2
 Piskeiy Teshuvos 2/3 based on Ashel Avraham Butchach 2, Vetzaruch Iyun as the allowance of the Ashel Avraham is based on the fact that one of the clothing is a minority of the other clothing, as understands Miaseif Lechol Hamachanos 2/12, and hence if the two clothing are the same size, such as two socks, or two sleeves, how would this allowance apply according to the Ashel Avraham.
Other Poskim: Some Poskim are stringent in the above matter. [Yayin Tov 11; Rivivos Efraim 1/4]
 Arizal ibid, brought in Kaf Hachaim 2/6; See also Ateres Rosh p. 30
 Gemara Brachos 51a brought in M”A 4/1; M”B 4/2; Darkei Chaim Veshalom 13 would not even allow someone to pass him his towel; Divrei Yatziv 1/2; Piskeiy Teshuvos 2/5
 Brachos 51a due to danger of Mazikin
 Darkei Chaim Veshalom 13; Piskeiy Teshuvos 4/5
 Darkei Chaim Veshalom 13; See Ashel Avraham Butchach which leaves this matter in question
 Piskeiy Teshuvos ibid