1. Question: [Friday 18^th Tamuz 5780]

May one sleep in his clothing or should he wear pajamas according to Halacha?

Answer:

There is no Halachic obligation for one to wear pajamas at night, and hence he can choose to sleep with his clothing, even though this is not the normal way of the world [seemingly due to reasons of comfort]. Nonetheless, some Poskim write that one should abstain from sleeping with one’s clothing. Whatever the case, it is proper for one who slept in his clothing to change clothing upon awakening prior to saying the morning blessings in order so he can say the blessing of Malbish Arumim according to all opinions. However, there is no problem to Daven in these clothing so long as they are kept clean, although some Poskim rule that one should never Daven with clothing that he slept in, and therefore also not sleep in clothing that he plans to Daven in, as perhaps he saw Keri at night and dirtied his clothing.] Likewise, it is recorded in Sefarim that one should not sleep with his shoes on, and nor should he sleep with metal attached to him, such as a belt. [The Poskim  record that in reward for the trouble that one goes through to remove his clothing at night and replace them in the morning, his sins are diminished.]

Sources: See Admur 317:1 “Velo Poshtim Malbusheihem”; Shut Min Hashamayim 12; Setimas Kol Hapsokim except Kitzur SHU”A; See Minhagei Chasam Sofer 1:44; Kitzur SHU”A 71:5 “One should take off his clothing and not sleep in them”; Yifei Laleiv 239:3; Meil Tzedaka 856; See regarding shoes: Yuma 78b regarding shoes, that one who sleeps in them tastes death, Chida in Avodas Hakodesh Tziporen Shamir 7:112  regarding metal and Piskeiy Teshuvos 239:14 regarding shoes and metal; Likkutei Maharich that sleeping with shoes it is Kasha for Shichicha; See here regarding malbish arumim https://shulchanaruchharav.com/halacha/must-one-receive-the-pleasure/