In earlier installments, we noted the Arizal's teaching that one should not put on two articles of clothing simultaneously – such as putting on a hat with the Kippa inside it – as this could cause a person to forget his Torah knowledge. The reason, as we discussed, is that the inner garment will be concealed and thus unable to receive the "Or Ha'makif" ("supernal light") that surrounds our clothing to protect them from harmful spiritual forces.
It would seem, at first glance, that this is relevant only to putting two garments on at the same time, because it is then when we want the "Or Ha'makif" to surround the garments. When removing garments, however, there appears to be no reason not to remove two garments simultaneously – such as removing a sweatshirt together with the shirt underneath it. This is, indeed, the position taken by Rav Shlomo Zalman Auerbach (Jerusalem, 1910-1995). He writes that when it comes to behaviors which could lead a person to forget his Torah knowledge, we have no reason to be stringent beyond the restrictions mentioned in the earlier sources. Since the sources speak only of the dangers of putting two garments on at the same time, we do not need to be concerned about removing two garments at the same time.
By contrast, the Yosef Ometz ruled stringently, that one should avoid also removing two garments at the same time.
Hacham Ovadia Yosef concluded that although Rav Shlomo Zalman's lenient ruling seems correct, nevertheless, it is preferable to act stringently and avoid removing two garments at the same time, because one might then also put them on together. If, for example, a person removes his shirt together with his sweater, and the shirt remains inside the sweater, he might later put them both on simultaneously, and so he should preferably remove his garments one at a time.