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A person must prepare himself for prayer, feel awe towards God’s majesty and glory, and be happy that he is about to stand before the King of Kings in prayer. This should also be apparent in his dress; one’s clothes should be respectable, fitting for one who stands before the King.
Men are obligated to cover their heads while praying, while reciting the name of Heaven, and before entering a synagogue (Shulchan Aruch 91:3). However, in practice, based on the custom accepted in Judaism, men are careful to wear a kippah (yarmulke) all day long (Shulchan Aruch 2:6). In any case, the obligation to wear a kippah while praying, when reciting God’s name, and while in a synagogue is greater, for it is rooted in law and not just in custom. 3
Additionally, although there are those who say that single women must also cover their heads while praying and reciting berachot, it is customary for women not to be strict about this. 4
One should wear a belt while praying, for the belt creates a division between one’s upper body, including the head and heart, and one’s ervah (nakedness). In that regard, prayer is superior to other matters of sanctity, for concerning other matters of sanctity it is unnecessary to wear a belt specifically, rather any separation between one’s heart and one’s nakedness is acceptable. Therefore anyone wearing underwear has a divider between his heart and his ervah. However, out of respect for the prayer service, it is a mitzvah to wear a belt, for that is the respectful way to pray, as it is written (Amos 4:12), "Israel, prepare to meet your God." Nevertheless, someone who normally walks around the whole day without a belt need not put one on before praying.
It is an extra pious act to always put on a belt for prayer because a belt signifies the separation between the lofty side of a person, comprised of the brain and the heart, and the lowly part of a person, containing his ervah and legs. Most people are deeply involved in their bodily desires, their brains and hearts occupied solely with matters of the moment and materialism. However, the Jewish people, who received the Torah from Heaven, are capable of overcoming their baser inclinations. They can direct their minds and hearts to superior matters, subsequently returning to the world of materialism and action in order to repair it. That is what the belt worn during prayer represents. The Chachamim even instituted a special berachah concerning this in the morning blessings – "Ozer Yisrael bigevurah" ("Who girds Israel with strength"). This explains why Chassidim enhance the mitzvah by wearing a special belt for prayer (a gartle). 5
4. The Appropriate Dress for Prayer
A person who finds himself in a situation in which he has no clothes is obligated to wear at least shorts and an undershirt for prayer (Berachot 25a; Shulchan Aruch 91:1). Although while reciting Shema and berachot it is sufficient, b’dieved, to only cover one’s ervah (Shulchan Aruch 74:6), while praying the Amidah before the King, one must at least cover his ervah and his heart (meaning, his front and back). 6
All this is b’dieved, but l'chatchilah one should enhance the mitzvah by wearing respectable clothing for prayer, so that one show at least as much honor to God as he does to human beings. Just as a person is careful to wear dignified clothing when meeting important people, so too, he must dress at least as respectably before praying. Indeed, a person who goes out once in his life to greet a king makes sure to wear his nicest clothing. However, a person who sees the king every day does not wear his fanciest garments; but he does make sure to wear clothes that suit his profession and status. Similarly, we come before the King three times a day, and we therefore dress nicely for prayer, but we save our finest apparel for Shabbatot, festivals, and joyous celebrations.
Everything depends on the custom of the place and the person. There are communities where everyone is accustomed to wearing a suit and hat to significant events, and thus they are required to dress that way for prayer as well. Likewise, in a place where it is not accepted to appear before important people in sandals without socks, certainly one must wear socks with his sandals while praying as well. Yet in places where people usually walk around in sandals without socks, and do not wear ties and hats even when approaching important people, they need not adopt different garb for prayer (based on Shulchan Aruch 91:5).
However, praying in a minyan is more important than wearing respectable clothes. Therefore, if someone who usually prays in a suit and hat finds himself in a situation in which going to his house to bring his suit and hat will cause him to miss praying in a minyan, it is better that he pray in simple attire in a minyan, for the mitzvah to pray in a minyan takes precedence over enhancing the mitzvah by wearing nice clothing (Avnei Yashfeh 1:7).
If one is wearing disgraceful clothes, normally not worn on the street, such as dirty work clothes or shorts which he put on to work in his yard, it is better that he change his clothes, even if he will miss praying with a minyan. If he wears such clothing to pray, he will offend the respect of Heaven. Additionally, there is concern that he will not be able to concentrate on his prayer, since he will be thinking that everyone is staring at his disgraceful dress.
5. Detailed Laws of One’s Dress for Prayer
Those whose profession requires them to wear work clothes and it is difficult for them to change before praying are permitted to pray in their work clothes, because for them, these articles of clothing are not considered disgraceful. Nevertheless, in situations in which they have time to change their clothes, they should try to come to prayer in more respectable attire.
One should not pray in pajamas (Mishnah Berurah 91:11). However, a person who is ill is permitted to pray in pajamas, because it is accepted that one who is not feeling well wears pajamas, even when important people come to visit him.
One should not stand in prayer wearing a raincoat, boots and gloves, because that is not the way to stand in front of important people (Mishnah Berurah 91:12). Yet, when it is very cold, it is permissible to pray in a raincoat and gloves, because this does not offend the respect due to prayer. Additionally, in a place where everyone regularly wears boots, one may wear them while praying.
Young boys and members of kibbutzim, who regularly walk around in shorts, even when important people come to visit them, are permitted to pray in that manner. However, the chazan must cover his legs until below the knee, because a person who wears shorts is called a poche’ach and is not allowed to lead the prayer service (see chapter 4:4).
Sometimes, a person is in a place where people normally dress less formally, such as a vacation spot; there, even those who always wear suits may wear just shirts without a jacket. In such a situation, whoever is not embarrassed to walk around without a suit, even before distinguished people, may also pray that way.
^ 3.A person whose kippah fell off and was blown to a distance farther than four amot may cover his head with his hand while walking to pick it up. However, while praying and reciting berachot it is not enough merely to cover one’s head with one’s hand. Since he is obligated to cover his head, one part of his body cannot be used to cover another part; although his friend’s hand may be used (Shulchan Aruch 91:4; Mishnah Berurah 91:10; Mishnah Berurah 6:11-12). Concerning the size of one’s kippah: the Igrot Moshe Orach Chaim, part 1, 1, writes that one can fulfill his obligation by wearing a kippah that does not cover the majority of his head even when saying Hashem’s Name. By contrast, the Or L’Tzion, part 2, 7:13 and Yabia Omer, part 6, 15:5 write that when praying and mentioning Hashem’s Name, which by law requires a head covering, one must wear a kippah that covers the majority of one’s head. Nonetheless, in practice, one who is lenient has on whom to rely, since it is a rabbinic ruling and regarding rabbinic rulings, the halachah follows the lenient opinion. Furthermore, in Masechet Sofrim 14:15 there is a dispute concerning whether or not one is obligated to cover one’s head when reciting a berachah. Or Zarua, part 2, 43, writes that the custom of our ancestors in France was to recite berachot bareheaded. Although according to most poskim the halachah is that we are obligated to cover our heads while reciting a berachah, in any case, the lenient opinion is incorporated to strengthen the opinion expressed in Igrot Moshe. Even so, it is good to be stringent out of respect for the prayer service. Moreover, if one wears a larger kippah during the prayer service, this is likely to cause a person to wear it throughout the whole day, thereby sanctifying God’s Name and accepting the responsibility to observe the Torah and mitzvot.
^ 4.Shut Ish Matzliach 1:24-25 obligates women just the same as men in terms of head covering when reciting God’s name. The Yabia Omer, part 6, 15 writes that single women should not be prevented from reciting a berachah bareheaded; however, it is proper for them to cover their heads while praying. As we already learned in the previous note, there are even those who say that there is no obligation for a man to cover his head while praying and mentioning God’s name. Since it is a rabbinic ruling, and it is customary for women to be lenient regarding this matter, they need not change their practice. Tzitz Eliezer 12:13 writes that according to the minhag, women do not need to cover their heads. He cites the explanation given by the Chatam Sofer that since gentile women were accustomed to cover their heads in their houses of worship, there is reason to refrain from practicing as they did. All this may be further studied in Peninei Halachah, Tefillat Nashim, 10:6, note 6.
^ 5.The Rishonim are divided into three opinions. The Terumah, Ran, and Hagahot Maymoniyot maintain that no matter what the situation, one must wear a belt while praying. In contrast to them, Rashi holds that one need not wear a belt at all for prayer; rather the important thing is that there be a divider between one’s heart and his ervah. The intermediate opinion is that of Rabbeinu Yerucham who maintains that one who normally wears a belt the whole day must also wear one while praying. So it is written in Shibolei Haleket 17, in the name of Rav Sa’adyah Gaon, as well as in Magen Avraham 91:1, whom many Acharonim cite as the way to practice. From the Shulchan Aruch 91:2 it can be inferred that he rules according to the stringent opinion, which is how the Mishnah Berurah 91:4 is inclined to rule as well. In any case, the minhag is according to those who are lenient, and since it is a rabbinic ruling, the ones who are lenient have the advantage. The Or L’Tzion, part 2, 7:13 explains that in the past when people wore robes without belts, they looked unkempt, but today we wear pants, and therefore it is unnecessary to be stringent regarding this. Hence, it is an extra pious act to be careful to always wear a belt while praying. The Chassidim enhance the mitzvah even more by wearing a special belt for prayer.
^ 6.B’dieved, if he mistakenly prayed without an undershirt, as long as he covered his ervah he fulfilled his obligation. However, the Acharonim disagree as to whether or not a person who does not have an undershirt should pray l'chatchilah. The Bei’ur Halachah 91:1, s.v. "Yatza" maintains that he may not. The Kaf HaChaim 3 is inclined to agree with the Levush who rules that he should pray since he is considered to be in circumstances beyond his control (annus).