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5. Wearing Shabbos hats, sun hats, baseball caps etc. on Shabbos:
A. Wearing a hat with an extension for protection purposes:
First opinion-Is forbidden if extension is a hard material: A large hat which is placed on one’s head in order to shade ones face, to protect it from the sun, or to protect it from flies and any case of the like in which one intention in wearing it is to for it to hover over him to protect him from a certain matter, then it is forbidden to wear it on Shabbos, even inside one’s house due to the making an “Ohel” prohibition. [This however only applies] if it extends past one’s head [the measurement of] one handbreadth [in width] by one handbreadth [in length], (even if [the extension] is only opposite ones face). [Likewise] however this [prohibition] only applies if (this) extending handbreadth is hard and strong and [thus] does not bend over downwards.
If it is a soft bendable material: However if it does bend over downwards, then even if it extends a lot more than a handbreadth around one’s entire head, then it is not defined as a “Ohel”, and is [thus] permitted.
Spreading a Tallis over one’s head: It is therefore permitted to spread the Tallis on one’s head even though it extends a lot past ones head, with exception to if it is made from a hard material cloth (called Grub Green) [in which case it would be forbidden to wear it on Shabbos for protection purposes]. [Thus, those that avoid wearing the Tallis on their head because of the Ohel prohibition, do not have upon whom to rely in their stringency, and it has no reasoning or source.]
Second Opinion-extension must be as hard as a roof to be forbidden: There are opinions which say that it was only prohibited [to wear a hat with a hard extension] if it is very hard like a roof (in which case it cannot easily be bent [and] therefore it is considered an Ohel. However, if it is merely very hard [but not like a roof] then it is not defined as an “Ohel” and is permitted [to be worn].)
Third opinion-Extension must be flat to be forbidden: There is an opinion which is even furthermore lenient that if [the extension of the hat] is not standing flat but rather is slanted, then it is not defined as an “Ohel” and is permitted [to be worn] even if [the extension] is very hard [like a roof].
The Final Ruling: It is proper to be stringent (in all the above [disputes] that [the extension] be actually drooping below on its own [as opposed to merely slanting, or drooping when applying force], in which case even if he then lifts [the dropping extension] and sets it up flat with his hands, it is Halachically meaningless).
Fourth opinion-Those which are lenient to wear even very hard hats for protection: In those places which are accustomed to be lenient in all cases [to wear felt hats, which have a very hard material extension and would thus be forbidden according to all the above mentioned opinions], even when the person intends [to wear it] as a tent [hovering for protection], one should not protest their actions being that they have upon whom to rely, as there are opinions which completely allow [wearing hats] in all cases, as they hold that there was no decree made here [against wearing this hat] due to [the] making a tent [prohibition] since it is being done in a way of wearing.
B. Wearing a hat with an extension not for protection purposes:
All the above [discussion of prohibition] is only if the person intends [to wear it] for it to hover over him to protect him from something. However, if his intentions are simply to cover his head, then although it inevitably forms a hovering around him, it is Halachically meaningless, as any Ohel/hovering which does not have walls under it contains no prohibition in being made unless ones intentions are to do so to make a tent [i.e. a hovering of protection], as will be explained in chapter 315 [Halacha 9 and 11].
Example-Wearing the accustomed felt hat: It is therefore permitted to wear a large felt hat which is accustomed [apparel] in some places, which [these hats] are called (Brital), even if they contain hard paper which due to this makes it very hard and it stands flat, being that one does not intend [to wear it] as a tent [hovering of protection] but rather in order to cover his head.
It is forbidden to wear a hat on Shabbos even in one’s house if all the following conditions apply:
1. It extends past one’s head 1×1 handbreadth. [Such as typical baseball caps].
2. One intends to wear it for protection purposes, such as to provide shade over his face, and not as a mere head covering.
3. The extension is made of a hard material which does not bend down on its own. [If it is as hard as a roof and is flat then it is forbidden according to all. If it is slanted or is not as hard as a roof, then it is disputed, and we are stringent.]
– Those which are lenient to wear hats, despite fulfilling the above conditions, do not need to be protested against doing so as they have upon whom to rely.
– If any of the three conditions are not fulfilled it is permitted to wear such a hat on Shabbos.
– The above only relates to wearing the hat inside one’s house or in an area with an Eiruv, regarding wearing it outside by an area without an Eiruv-See chapter 301 Halacha 50.
May one wear a baseball cap on Shabbos?
One may wear it if his intent is not to do so for shade. However, those that are lenient to wear it for shade do not need to be protested.
May one wear a Shabbos hat?
May one wear a Shabbos hat if his intent is also for protection from the sun?
This matter requires further analysis.
May one put his Shabbos hat on while sitting in his room in order to protect him from the sun?
May one wear a Tallis over his hat?
May one place a plastic hat rain cover on a hat on Shabbos?
It is permitted to put on a rain cover onto one’s hat on Shabbos and doing so does not pose an Ohel prohibition. This applies whether the cover is special manufactured hat rain cover or one is using a plastic bag. The following will discuss if one may walk with this hat cover in an area without an Eiruv:
Area without Eiruv: Some Poskim rule it is forbidden to wear a rain cover for a hat in an area without an Eiruv even if the rain cover is manufactured for this purpose. Other Poskim rule it is permitted to wear a rain cover that is manufactured for hats even if one will be walking in an area without an Eiruv. Practically, even those that are lenient are only to do so with a manufactured hat rain cover and not through placing a plastic bag over the hat, in an area without an Eiruv. Those who are careful not to carry even in an area with an Eiruv may be lenient in this regard to wear a hat rain cover.
 Admur 301:48; Michaber 301:40; Shabbos 138b
 First opinion in Admur ibid; Michaber ibid
 Admur ibid; M”A 301:51; Taz 301:27; M”B 301:152
 Admur ibid; Michaber ibid; Tosafus on Gemara ibid
 Admur ibid; Michaber ibid writes simply one handbreadth.
 Admur ibid; M”B 301:151; Gemara ibid
 Admur ibid; M”B 301:151; Gemara ibid
 Admur ibid; M”A 301:51; M”B 301:151; Gemara ibid
 M”B ibid
 Admur ibid; M”A 301:51
 Rambam 22:31
 Admur ibid; M”A 301:51; M”B 301:152
 Sefer Hateruma 254; Hagahos Maimanis
 Admur ibid; It seems the M”A ibid rules one may be lenient by hats like the second and third opinion and he hence suggests that even if the hat is as hard as a roof, one can simply bend it down and then it may be worn even for protection purposes.; It is unclear how the M”B himself holds regarding all the leniencies that he recorded.
 Lit. good
 Admur 301:49; M”A 301:51 in name of Bach; M”B 301:152 in name of Elya Raba
 Rashi Shabbos ibid
 Admur 301:48; M”A 301:51; Taz 301:27; M”B 301:152
 Admur 301:49; Taz 301:27; M”B 301:152
 Felt is a non-woven cloth that is produced by matting, condensing and pressing woolen fibers. While some types of felt are very soft, some are tough enough to form construction materials. Felt can be of any color, and made into any shape or size.
 M”A 301:51; M”B 301:152
 Brought in M”A ibid; M”B ibid and negated, but so defends the Machatzis Hashekel ibid, stating that so he saw done even by Gedolim.
 The reason: As the Ohel prohibition does not apply in a case that there is not a Tefach of space between the cover and the hat. [Admur 315:19; 315:12; 640:10; Michaber 315:13; Rambam 22:23] B) A hovering made to protect an item [in contrast to a human] does not have the status of an Ohel when covering an item less than the size of a barrel. [See Admur 315:19 regarding a barrel]
 Piskeiy Teshuvos 301:6 [old] 301:20 [new]
 Minchas Yitzchak 3:26; Igros Moshe 1:108-110; Mahariy Shteif 73 and 124; Dvar Yehoshua 2:129; Betzel Hachochmah 2:80; Or Letziyon 2:23-3; Poskim in Piskeiy Teshuvos ibid footnote 144
 The reason: As a hat rain cover is not considered a clothing but rather a rain protector, and one hence transgresses carrying an item on Shabbos even when worn. It is thus unlike the allowance brought in Admur 301:11 and 43 which allows wearing one hat on top of another due to the rain, as that case refers to a hat that is wearable during the week even not during rain, unlike our case where the hat is unwearable during non-rain times. It is rather similar to one who wears a cloth over his head to protect his scarf from rain in which case we rule it is considered a Masuiy, as it is not Derech Malbush. [See Admur 301:11]
 Chelkas Yaakov 1:99; Har Tzevi 1 Tal Harim Motzi 2; Shevet Halevi 1:61; Divrei Yatziv 1:147; Chesehv Haeifod 1:81 and 2:67; Beir Moshe 2:31; Az Nidbaru 1:71; 4:37; Bris Olam Motzi 10; Tzitz Eliezer 10:23; Tiferes Adam 2:11; SSH”K 18:10 in name of Rav SZ”A regarding Karmalis; Mishneh Halachos 2:72; 6:72; Yabia Omer 5:24; 9:108-146; Poskim in Piskeiy Teshuvos ibid footnote 145
 The reason: As one may wear one hat on top of another on Shabbos even simply to protect from rain [Admur 301:11 and 43] and this hat cover is considered a clothing being that it is made to the same fit as a hat and is worn as a Derech Malbush. [Shevet Halevi and Poskim ibid] Likewise, it is also worn to protect the person from rain, in which case we rule one may cover the hat even if it is not a true clothing being that it is worn as a Derech Malbush. [See Admur 301:11]
 Piskeiy Teshuvos ibid; See Piskeiy Teshuvos ibid footnote 148 for Poskim who are lenient even in such a case
The reason: As no one walks outside with a plastic bag covering them, and hence it is not considered a Malbush even when used as such. [See Admur 301:43]
 Piskeiy Teshuvos ibid footnote 147