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One should not wear clothing which is dirty, lest he be disparaged in the eyes of others.
Not to be dressed sloppy:
It is proper [for every person to be careful] to dress and look decent in order so he not appear degrading in the eyes of others.
Wearing a shirt inside out: Due to the above one should be careful not to wear his shirt [or other clothing] the wrong way, inside out. If the person was not careful and he wore the shirt inside out, then if he is a Torah scholar, he must remove his shirt and re-wear it correctly.
Must one be careful not to wear the clothing inside out if others cannot notice?
- Example: If there are no visible threads on the inside may one wear the shirt inside out? If one put his undershirt inside out and is wearing a shirt over it must he still turn it over?
Some rule one may wear it inside out if there are no visible or degrading changes that are visible to the public. Thus undergarments do not have to be turned over. Others however rule based on Kabala that one must be careful to always wear the clothing properly, even if they are not visible, and so can be implied from Admur.
May socks; Tzitzis; belt; Yarmulke be worn inside out?
All clothing that one is not particular in which way they are worn, and hence sometimes he wears it one way and another time the other way, is not considered to have an inside or outside and is hence not relevant to the above law. Some actually received a tradition that wearing the Yarmulke inside out is a Segula against headaches, and so is practiced by certain Tzaddikim.
 Kitzur Shulchan Aruch 3 brought in Ketzos Hashulchan 3/3
 Kama 2/2; Basra 2/3; See Alef Lamagen 3 for a thorough analysis from Talmud and Rishonim regarding this law
 Lit Tov
 Kama 2/2
 Basra 2/3
 See Perisha 2/3; Olas Tamid 2/1; Kaf Hachaim 2/4 that this refers to an undershirt and the reason why “Chaluk/shirt” was specifically mentioned in this Halacha is because it refers to an undershirt and thus the novelty is that even though [it is covered] and is a great trouble to remove all one’s clothing and turn it over, nevertheless one must do so. [ibid]
 Basra ibid
 As in such a case the inner stitches [and threads-Basra] are visible and debasing to the person when he is in front of others. [ibid]
 This ruling of Admur is based on Taz 2/2. If one is not a Torah Scholar then there is no need to remove the shirt, although initially one is to wear it the right way. [Taz ibid; Perisha 2/3] The reason why specifically a Torah Scholar must be careful in this is because he must show respect for that which he represents. Regarding this matter every person can consider himself a Torah Scholar. [Olas Tamid 2/1]
Other Opinions: Some Poskim rule that every person must remove the shirt and wear it the right way. [Birkeiy Yosef 2/1; Tevuas Shur brought in Alef Lamagen ibid]
 As otherwise he will be included within “All my haters love death” [Mishleiy 8/36], as people will say “how degrading Torah learners are”. [Kama ibid] In order not to be included within “my haters”. [Basra ibid]
 See Alef Hamagen 3 [towards end of Teshuvah]; Hagahos Taharas Hashulchan
 Seder Hayom; Ashel Avraham Butchach 2 [Mahadurah Tinyana]; See Perisha; 2/3; Olas Tamid; 2/1; Kaf Hachaim 2/4 that the reason why “Chaluk/shirt” was specifically mentioned in this Halacha is because it refers to an undershirt and thus the novelty is that even though [it is covered] and is a great trouble to remove all one’s clothing and turn it over, nevertheless one must do so.
The reason: It can damage memory, perhaps just like placing two clothing on simultaneously. [Ashel Avraham ibid]
 This is implied from Basra 2/3 which adds the Halacha of not placing on two clothing simultaneously to the end of this Halacha. Seemingly they have no connection, and in Kama 2 Admur in truth placed it in two different Halachos. Likewise in Basra ibid [as opposed to Kama] Admur omitted the reason as people will say “how degrading Torah learners are” thus implying it should not be done even if it is not noticeable. Vetzaruch Iyun.
 Ashel Avraham Butchach 4 [Mahadurah Tinyana]
 Piskeiy Teshuvos 2 footnote 23
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