Kippah: Can't live without it

(ה) תִּקּוּן הַמַּלְבּוּשִׁים כֵּיצַד. מְתַקֵּן מַלְבּוּשָׁיו תְּחִלָּה וּמְצַיֵּן עַצְמוֹ וּמְהַדֵּר שֶׁנֶּאֱמַר הִשְׁתַּחֲווּ לַה׳‎ בְּהַדְרַת קֹדֶשׁ. וְלֹא יַעֲמֹד בִּתְפִלָּה בַּאֲפוּנְדָתוֹ, וְלֹא בְּרֹאשׁ מְגֻלֶּה, וְלֹא בְּרַגְלַיִם מְגֻלּוֹת אִם דֶּרֶךְ אַנְשֵׁי הַמָּקוֹם שֶׁלֹּא יַעַמְדוּ בִּפְנֵי הַגְּדוֹלִים אֶלָּא בְּבָתֵּי הָרַגְלַיִם. וּבְכָל מָקוֹם לֹא יֶאֱחֹז תְּפִלִּין בְּיָדוֹ וְסֵפֶר תּוֹרָה בִּזְרוֹעוֹ וְיִתְפַּלֵּל מִפְּנֵי שֶׁלִּבּוֹ טָרוּד בָּהֶן. וְלֹא יֶאֱחֹז כֵּלִים וּמָעוֹת בְּיָדוֹ. אֲבָל מִתְפַּלֵּל הוּא וְלוּלָב בְּיָדוֹ בִּימוֹת הֶחָג מִפְּנֵי שֶׁהוּא מִצְוַת הַיּוֹם. הָיָה מַשּׂוֹי עַל רֹאשׁוֹ וְהִגִּיעַ זְמַן תְּפִלָּה אִם הָיָה פָּחוֹת מֵאַרְבָּעָה קַבִּין מַפְשִׁילוֹ לַאֲחוֹרָיו וּמִתְפַּלֵּל בּוֹ. הָיָה אַרְבָּעָה קַבִּין מַנִּיחוֹ עַל גַּבֵּי קַרְקַע וְאַחַר כָּךְ יִתְפַּלֵּל. דֶּרֶךְ כָּל הַחֲכָמִים וְתַלְמִידֵיהֶם שֶׁלֹּא יִתְפַּלְּלוּ אֶלָּא כְּשֶׁהֵן עֲטוּפִים:

(5) Adjustment of the dress. Before beginning the Service, the dress should first be adjusted and the personal appearance made trim and neat, as it is said, "O worship the Lord in the beauty of holiness" (Psalms 96:9). One should not stand in prayer wearing a moneybelt, nor bareheaded, nor barefoot, where the local custom is not to stand in the presence of the great, without shoes. And one should not pray anywhere, holding phylacteries in the hand or carrying a scroll of the law in the arms, for the mind would then be preoccupied with those sacred objects. Nor while praying, should vessels or money be held in the hand. On the feast of Tabernacles, however, the worshiper prays, while carrying a palm branch—this being the religious duty of the day. When the time comes to recite the prayer, a person carrying a burden on his head, adjusts it behind him, if it is less than four kabs**A kab is equal in volume to 4 logs. A log is equal in volume to 6 hen’s eggs. and recites the prayer. If it is four kabs in size, he places it on the ground, and then prays. The practice of all the sages and their disciples is not to pray unless their heads are wrapped in the Talith (praying shawl).

ומותר בנשים ובקטנים שאין נקראין שחורי הראש אלא אנשים מאי טעמא אנשים זימנין דמיכסו רישייהו וזימנין דמגלו רישייהו אבל נשים לעולם מיכסו וקטנים לעולם מיגלו
The mishna states: But he is permitted to derive benefit from women and from children, because only men are called: Those with dark heads. The Gemara explains: What is the reason for this? Men sometimes cover their heads and sometimes uncover their heads. They can be called dark heads since, for the most part, they have dark hair which is often uncovered. But women’s heads are always covered, and children’s heads are always uncovered, and the expression dark heads is referring to men whose hair is sometimes seen.
אלא רק ארק קשיא רק ארק נמי לא קשיא אפשר כדרב יהודה דאמר רב יהודה היה עומד בתפלה ונזדמן לו רוק מבליעו בטליתו ואם טלית נאה הוא מבליעו באפרקסותו רבינא הוה קאי אחורי דרב אשי נזדמן לו רוק פתקיה לאחוריה א"ל לא סבר לה מר להא דרב יהודה מבליעו באפרקסותו א"ל אנא אנינא דעתאי:
However, The contradiction between spitting in the case where Rabbi Yehuda HaNasi did so and spitting where it is deemed tantamount to spitting in the face of the king is difficult. The Gemara replies: The contradiction between spitting in one case and spitting in the other case is also not difficult, as it is possible to resolve it in accordance with the opinion of Rav Yehuda, as Rav Yehuda said: One who was standing in prayer, and saliva happened to accumulate in his mouth, he absorbs it in his garment. And if it was a fine garment and he does not want it to become sullied, he may cover it up in his head covering. That way, one is permitted to spit. The Gemara relates: Ravina was standing behind Rav Ashi during prayer when saliva happened to accumulate in his mouth, so he discharged it behind him. Rav Ashi said to him: And does the Master not hold in accordance with that statement of Rav Yehuda, who said that one absorbs it in his head covering? He said to him: I am delicate, and the mere knowledge that there is spittle in my head covering disturbs my prayer.
רבי חייא בר אבא אשכחיה לריב"ל דשדי דיסנא ארישיה וקא ממטי ליה לינוקא לבי כנישתא א"ל מאי כולי האי א"ל מי זוטר מאי דכתיב והודעתם לבניך וסמיך ליה יום אשר עמדת לפני ה' אלקיך בחורב מכאן ואילך רבי חייא בר אבא לא טעים אומצא עד דמקרי לינוקא ומוספיה רבה בר רב הונא לא טעים אומצא עד דמייתי לינוקא לבית מדרשא
The Gemara relates: Once Rabbi Ḥiyya bar Abba encountered Rabbi Yehoshua ben Levi, and saw that he had placed an inexpensive covering on his head and brought his child to the synagogue to study. Rabbi Ḥiyya bar Abba said to him: What is the reason for all this fuss, as you are in such a hurry that you do not have time to dress yourself properly? Rabbi Yehoshua ben Levi said to him: Is it insignificant, that which is written: “But make them known to your sons,” and juxtaposed to it is the phrase in the verse that states: “The day when you stood before the Lord your God in Horeb”? The Gemara comments: From this moment onward, Rabbi Ḥiyya bar Abba would not taste meat [umtza], meaning he would not eat breakfast, before he had read to his child and added to the child’s studies from the day before. Similarly, Rabba bar Rav Huna would not taste meat before he had brought his child to the study hall.
תני חדא צורר אדם תפיליו עם מעותיו באפרקסותו ותניא אידך לא יצור
It was taught in one baraita: One may bundle his phylacteries with his money in his head covering [apraksuto], and it was taught in another baraita: One may not bundle phylacteries and money together.
זכה עושין לו צלצל לא זכה עושין לו ענק שנאמר (משלי א, ט) וענקים לגרגרותיך זכה עושין לו ענק לא זכה עושין לו קמיע שנאמר (איוב מ, כט) ותקשרנו לנערותיך
If one is deserving at least of this reward, a covering is prepared for him, and if one is not deserving, a necklace is prepared for him, as it is stated: “And necklaces about your neck” (Proverbs 1:9). If one is somewhat deserving, a necklace is prepared for him, and if one is not deserving even of this, only an amu-let is prepared for him from the skin of the leviathan, as it is stated: “Or will you bind him for your maidens” (Job 40:29), i.e., a small amulet is prepared for him, like the amulets tied on children’s necks.
א"ר יעקב א"ר יוחנן לא שנו אלא שאין לו מנעלים ברגליו אבל יש לו מנעלים ברגליו מנעליו מוכיחין עליו
Rabbi Ya’akov said that Rabbi Yoḥanan said: They taught that a mourner is required to remove his head covering on Shabbat only when he has no shoes on his feet, so that he not appear too obviously to be in mourning. But if he has shoes on his feet, then his shoes prove that he is not observing the rites of mourning on Shabbat.
אמר שמואל פח"ז חובה נת"ר רשות
Shmuel offered a mnemonic device with regard to the observance of mourning rites on Shabbat, and said: Peh, ḥet, zayin are obligatory. These letters combine to create a mnemonic standing for: Uncovering the head [periat rosh], reversing the torn garment [ḥazarat kera], and standing the bed upright [zekifat hamitta]. However, nun, tav, reish, which stand for: Wearing shoes [ne’ilat hasandal], marital relations [tashmish hamitta], and hand washing [reḥitzat yadayim], are optional.
פריעת הראש חזרת קרע לאחוריו זקיפת המטה חובה נעילת הסנדל תשמיש המטה רחיצת ידים ורגלים בחמין ערבית רשות ורב אמר אף פריעת הראש רשות
This is explained: Uncovering the head, i.e., removing the head covering usually worn by a mourner; reversing the tear to the back, so that it will not be visible; and standing the bed upright in the usual position, so that it is not overturned, are all obligatory for the mourner to uphold in honor of Shabbat. However, wearing shoes, engaging in sexual relations, and washing one’s hands and feet in hot water in the evening are optional activities on Shabbat. If a mourner wishes to refrain from them he may do so. And Rav said: Uncovering the head is also an optional activity.
ושמואל מאי שנא נעילת הסנדל דרשות דלאו כולי עלמא עבידי דסיימי מסאנייהו פריעת הראש נמי לאו כולי עלמא עבידי דמגלו רישייהו
The Gemara asks: According to Shmuel, what is different about wearing shoes that it is optional? His reasoning presumably is that not everyone wears shoes at all times, and therefore not wearing shoes will not be perceived by others as a sign of mourning. If so, the same thing may be said about uncovering the head also, i.e., not everyone uncovers his head at all times, as some people always walk around with their heads wrapped. This, too, should not be seen as a clear display of mourning, and therefore uncovering one’s head should also be treated as optional.
רבינא הוה יתיב קמיה דר' ירמיה מדיפתי חלף ההוא גברא קמיה ולא מיכסי רישא אמר כמה חציף הא גברא א"ל דלמא ממתא מחסיא ניהו דגיסי בה רבנן
The Gemara cites another incident involving honor one demonstrates for his teacher. Once, when Ravina was sitting before Rabbi Yirmeya of Difti, a certain man passed before him and did not cover his head. Ravina said: How rude is this man, who does not show respect by covering his head in honor of a rabbi. Rabbi Yirmeya of Difti said to him: Perhaps he is from the city of Mata Meḥasya, where rabbis are common and the people living there are consequently not as careful to display honor as those in other places.
וּלְשָׁם מוֹצִיא כָל כְּלֵי תַשְׁמִישׁוֹ, וְלוֹבֵשׁ כָּל מַה שֶּׁיָּכוֹל לִלְבּשׁ, וְעוֹטֵף כָּל מַה שֶּׁיָּכוֹל לַעֲטֹף. רַבִּי יוֹסֵי אוֹמֵר, שְׁמֹנָה עָשָׂר כֵּלִים. וְחוֹזֵר וְלוֹבֵשׁ וּמוֹצִיא, וְאוֹמֵר לַאֲחֵרִים, בֹּאוּ וְהַצִּילוּ עִמִּי:
And thither [according to the first tanna, to a courtyard with an eiruv; according to Ben Betheira, even to a courtyard without an eiruv], he takes out all of his utensils [which he needs for that day's meals]. And he may clothe himself with whatever he can and cloak himself with whatever he can. R. Yossi says: Eighteen garments [that he is wont to wear on a weekday, and not more. They are: the outer cloak, a garment filled with sponge and cotton-wool between stitch and stitch, a broad belt worn above his garments, a short, narrow garment, an undershirt worn on one's flesh, a belt worn on that, a hat, a turban, two shoes, two socks, two gloves reaching to the armpits, two scarves for wiping himself, a small cloth for covering his head and shoulders, and his neck cloth with its two ends hanging down in front.] And he may return and clothe himself and carry out. And he may tell others: "Come and rescue with me." [For just (i.e., in equal measure) as he rescues, so do they — whereas above, he said: "Come and rescue for yourselves"; for sometimes he rescues more than they, as when he had not yet eaten and they have, or vice versa.]
לבושה לא בושה גלימא שנעשה בו כגלם גולתא גלי ואיתיב פוריא שפרין ורבין עליה בור זינקא בור זה נקי סודרא סוד ה' ליראיו אפדנא אפיתחא דין ת"ר שלשה כל זמן שמזקינין מוסיפין גבורה ואלו הן דג ונחש וחזיר:
An outer garment is called levusha, which is an acronym for lo busha, which means no shame, as one who is clothed is no longer ashamed. A broad outer garment is called gelima, an allusion to the fact that, by wearing it, one is transformed into an amorphous golem-like figure, as his limbs are indistiguishable. A beautiful coat is termed golta, which is an acronym for geli ve’eitiv, which means reveal, remove the coat, and only then I will sit, so that the coat will not get dirty. A bed is called purya, an allusion to the fact that people parin veravin, which means procreate, upon it. An empty pit is called bor zinka, which is an acronym for bor ze naki, which means that this pit is empty of water. The head covering of Torah scholars is called sudara, an acronym for sod yareh, which is a reference to the verse: “The counsel of the Lord is with them who fear Him [sod Hashem lire’av]” (Psalms 25:14). A palace is called apadna, which is an acronym for apitḥa dein, meaning: To this entrance all come. The Gemara cites an additional baraita related to the nature of the creatures. There are three creatures that grow mightier with age, and they are the fish, and the snake, and the pig.
ולולי שאינני רגיל לחלוק על הקדמונים א"ל שיש גדול שיסייעני הייתי נוטה להקל ולברך בגילוי הראש ואפילו לקרות ק"ש שרי שהרי איתא במדרש רבה אמר רבי ברכיה מלך ב"ו משגר פרוטגמא שלו למדינה מה הם עושין כל בני המדינה עומדים על רגליהם ופורעים את ראשיהן ורואין אותה באימה ביראה ברתת ובזיע אבל הקב"ה ית' אומר לישראל קראו ק"ש ברוטגמא דידי הרי לא הטרחתי עליכם לקרות לא עומדים ולא פרועי ראש כו' משמע להדיא דליכא איסור בפריעת ראש אלא שלא החמיר עליהם ומה אעשה שכבר הורו לאיסור.
If not for the fact that I do not usually dispute earlier authorities unless there is a great authority to support me, I would incline toward leniency and in favor of reciting blessings with an uncovered head. Even the recitation of Shema is permitted, for it states in Midrash Rabba (Vayikra §27): R. Berekhya said: A flesh-and-blood king sends his charter to the province, what do they do? All residents of the province stand up, uncover their heads, and read it with fear, awe, trembling, and perspiration. But the Holy One, blessed be He, says to Israel: Recite the Shema, My charter. I do not trouble you to read it standing or with your heads uncovered. This clearly implies that it is not forbidden to uncover one’s head; rather, He did not impose [an uncovered head] as a stringency. But what can I do? They have already ruled this to be forbidden.
תשובה אין אני יודע איסור לברך בלא כסוי ראש ומהרא"י פשוט לו שאסור בהזכרת שם בלא כיסוי הראש ולא ידענא ממאי והנה מצאתי שכתב במסכת סופרים יש בו מחלוק' שכתב פוחח הנראים כרעיו או בגדיו פרומים או מי שראשו מגולה ואינו רשאי להוציא הזכרה מפיו ע"כ ור' ירוחם כתב בסוף נתיב ט"ז שאסור לברך בגילוי הראש.
Response: I know of no prohibition against reciting a blessing without [wearing] a head covering. Yet it was obvious to Maharai (=R. Yisrael Isserlein) that it is forbidden to invoke God’s name without the head covered, and I do not know whence [he infers that]. Now I have found that it is written in tractate Soferim (14:15) that there is a dispute: “A shabby person whose knees are visible or whose clothing is torn, or one whose head is uncovered, may lead the prayers (“pores et ha-Shema”), but some say that one may lead with knees [showing] or torn clothes, but not with an uncovered head. And he may not let mention [of God’s name] leave his mouth.” R. Yeruham wrote at the end of §16 that it is forbidden to recite a blessing with an uncovered head.
אבל בזה תמיהני שנהגו איסור בפריעת ראש אף בלא תפלה ולא ידעתי מאין זה להם כי לא מצינו איסור בפריעת הראש כי אם לאשה כדאיתא בפ' המדיר וממידת חסידות הוא שלא לילך ד' אמות בגילוי הראש ודוקא הליכה ד"א (מו') כדאיתא בפר' כל כתבי א"ר חנינא תיתי לי דלא סגינא ד' אמות בגילוי הראש והוא ממידת חסידות כמ' שחשוב שם אינך תיתי לי כו' ועוד ראייה מפ"ק דקידושין שמסיק שם אמר ריב"ל אסור להלוך ד' אמות בקומה זקופה שנ' מלא כל הארץ כבודו רב הונא בריה דרב יהושע לא מסגי ד' אמות בגילוי הראש אמר שכינה למעלה מראשי משמע דוקא בקומה זקופה הוא אסור אבל בגילוי הראש אין בו איסור אלא דרב הונא החמיר על עצמו מכח מידת חסידות ועכשיו הוא להיפך בקומה זקופה אינם נזהרים ואדרבה הגאים והעשירים הולכים נטויי גרון ובגילוי הראש נזהרים לא מחמת חסידות אלא סוברים דת יהודית הוא.
Yet I am astonished that they treat uncovering the head as forbidden even when not praying. I do not know whence they derived this, for we find no prohibition against an uncovered head except in the case of a woman, as stated in the chapter “Ha-madir” (Ketubot 72b), and that it reflects piety (midat hasidut, i.e., not actually required by law) not to walk four cubits with an uncovered head. Yet this is specifically walking four cubits, as stated in the chapter “Kol Kitvei” (Shabbat 118b): “R. Hanina said: I deserve it, for I did not walk four cubits with an uncovered head.” This reflects piety, like all of the other examples of “I deserve” listed there. Further evidence is from the first chapter of Kiddushin (31a), which rules: R. Yehoshua b. Levi said: It is forbidden to walk four cubits with an upright posture, as it is stated: ‘The whole world is filled with His glory’ (Yeshayahu 6:3). R. Huna b. R. Yehoshua would not walk four cubits with his head uncovered. He would say: ‘The divine presence is above my head.’ This implies that specifically walking with an erect posture is forbidden, but it is not forbidden to do so with one’s head uncovered. Rather, R. Huna was stringent with himself, motivated by piety. Nowadays, the opposite is the case: they are not careful about avoiding an erect posture. On the contrary, the proud and the rich walk around with their heads held high, but they are careful about uncovering their heads—not because of piety, but because they think this is the Jewish religion.
עוד מצאתי כתוב הא דגלוי הראש כו' היינו באויר השמים דוקא וכן נראה לפרש הא דקומה זקופה אף שמלא כל הארץ כבודו מ"מ אינו נראה כאילו אינו משגיח בעושיהן כי אם מי שהולך באויר השמים ושם יש לו לזכות ולהתעורר אף שמהררא"י כתב שאין לחלק בין בית לחצר כי מלא הארץ כבודו היינו בהזכרת השם וכן מסתבר שמדת חסידות הוא בהזכרת השם שלא יהא בגילוי הראש כמו הולך ד' אמות באויר השמים וכן מצאתי כתוב בשם הר"ם שכל זה מידת חסידות אלא שהרי"ף כתב שיש למחות שלא לכנס בב"ה בגילוי וכן הטור לא כתב ויכסה ראשו אלא גבי תפלה ולא גבי ק"ש ומה אעשה שהעם נהגו בו איסור ואיני רשאי להקל בפניהם.
I have also found written that this statement about an uncovered head only applies out under the open sky. This is a reasonable explanation of the case of the erect posture—even though the entire world is filled with His glory, nevertheless, one does not look as though he is ignoring his Maker except when he walks out under the open sky. It is there that one must remember and maintain vigilance. And even though R. Isserlein wrote that there is no distinction between home and courtyard, for the whole world is filled with His glory, this only applies to the case of invoking God’s name. Indeed, it stands to reason that refraining from invoking God’s name with an uncovered head reflects piety, much like the case of walking four cubits in the open air. I have also found this written in the name of R. Meir [of Rothenburg], namely, that this is all a matter of pious practice, although R. Peretz wrote that one should object to someone entering the synagogue with an uncovered head. Moreover, Tur does not state “and he shall cover his head” except with regard to prayer, not with regard to the recitation of the Shema. But what can I do? The people practice this as a prohibition, and I have no authority to be lenient in their presence.
ושמעתי על חכם אחד כשהיה לומד היה לומד בגילוי הראש ואמר שכבד עליו המשא ומ"מ נראה בעיני אף שאין איסור בדבר ואף לא מידות חסידות כשאינו מזכיר השם מ"מ דת"ח יש לו להזהר מאחר שהעם תופסים בה לקלות ולפריצות כאלו עובר על דת יהודית ואפי' לומד בחדרו אין לסמוך על זה שמא העם הארץ יראה ויקל בו לא בחינם אמרו כל שאסור מפני מראית העין אפי' בחדרי חדרים אסור.
I have heard of a sage who would study Torah with his head uncovered, saying that the weight was too heavy for him. Nevertheless, it seems to me that although it is not forbidden, and it is not even an act of piety if one is not invoking God’s name, a Torah scholar should still be cautious, for the people perceive it as laxity and permissiveness, as though he transgressed the Jewish religion. Even if he is studying in his room, he should not rely on this, lest an ignoramus see him and make light of him. It is not for naught that they say that anything forbidden because of how it looks (mar’it ayin) is even forbidden in the innermost chambers.
ועכשיו אני אגלה את קלון האשכנזים בודאי מי ששותה יין נסך במלון של גוים ואוכל דגים מבושלים בכלי שלהם והמחטי' הוא שמאמין לפונדיקי' שלא בשלו בה אין חוששין עליו ואין בודקין אחוריו ונוהגין בו כבוד אם הוא עשיר ותקיף ומי שהיה אוכל ושותה בהכשר רק שהיה בגילוי הראש היו תופסין אותו כאלו יצא מן הכלל ע"כ החכם עיניו בראשו ידע להשמר שלא יתפסו עליו ואם כבד עליו להניח על ראשו דבר כבד יכסה ראשו בבגד פשתן דק או במשי.
Now I will disclose the shame of Ashkenazim. Certainly one who drinks libation wine (yeyn nesekh) in a gentile’s inn, and eats fish cooked in their vessels, and who is considered strict if he trusts the innkeeper’s wife when she says that she did not cook anything else in them, is not under any suspicion. We do not investigate him, and we treat him with respect if he is rich and powerful. But one who eats and drinks only kosher food, but he does so with his head uncovered, is perceived to be a deviant. Therefore, “the wise man has his eyes in his head” (Kohelet 2:14) and will know to protect himself so that they do not attack him. If placing something heavy on his head will weigh upon him, he should cover his head with a garment of fine linen or silk.
ומ"מ נראה אפי' מי שירצה לברך ברכת נהנין והוא בלילה שאין לו כובע עליו או כשרוחץ באמבטי די לו במה שמכסה את ראשו בידיו אף שגדול אחר העתיק לאיסור ומהררא"י הביאו וראייתו מר"ת שכשהיה רוחץ בחמין והיה שות' היה מתכסה בבגד כנגד לבו כו' משמע דוקא בבגד ולא בידים אין זה ראייה כי מה לא חשוב כיסוי שדרך האדם להניח ידיו על לבו והרואה לא יצא שצריך לכסות את הלב או ידמה לו שלא כסהו ממש כנגד הלב אבל למעלה מראשו שהוא דבר הניכר מספיק בכיסוי היד בפרט לפי מה שכתבתי שאין בו איסור כ"א חסידות מספיק לו כיסוי היד בפרטי באקראי בעלמא:
Still, it seems reasonable that even one who wishes to recite a blessing over consumption (Birkat ha-nehenin) at night, when he has no hat on, or while he is bathing, it is sufficient for him to cover his head with his hands, even though one major authority has recorded that this is forbidden, and R. Isserlein cites him. Their proof is that Rabbeinu Tam, when he was bathing in warm water and would drink, would cover himself with a garment over the place of his heart, not with his hands. But this is no proof, for the reason this is not considered covering is that it is normal for someone to place his hands on his heart, and one who sees this will not know that one needs to cover his heart, or will imagine that he did not really cover the area over the heart. However, since it is discernable, it is sufficient to use the hand as a cover above his head, especially given what I have written, namely, that this is not a prohibition but merely a matter of piety. It is therefore sufficient to use the hand as a cover in an impromptu fashion.
וע"ד המדרש דרך האתרים דרך התייר הגדול, הוא ארון ברית ה' הנוסע לפניהם דרך שלשת ימים לתור להם מנוחה. וי"א שהוא סיחון מלך האמורי, ונקרא כנעני כי כל אמורי כנעני. ודרשו רז"ל מה שמועה שמע, שמע שמת אהרן ונסתלקו ענני כבוד וזהו שכתוב ויראו כל העדה כי גוע אהרן, א"ר אבהו אל תקרי ויראו אלא וַיֵרָאוּ שעד עכשיו לא היו נראין לאומות, שהיו מכוסים בענני כבוד. וכן במדרש תנחומא, כיון שמת אהרן נסתלקו ענני כבוד ונראו כאשה שראשה פרוע.
A Midrashic approach based on Tanchuma Chukat 18: the word האתרים is an allusion to the “great traveler (spy),” i.e. the Holy Ark which was in the habit of traveling three days’ march ahead of the main body of the people in order to spy out (find a location) for the people to make camp (Numbers 10,33).
Some commentators feel that the king described here as the King of Arad was in fact Sichon the King of the Emorites and the reason he is referred to here as “the Canaanite” is that that every Emorite is also a Canaanite by definition.
Our sages in Rosh Hashanah 3 say that the news which the Canaanites had heard was that Aaron had died and that the protective clouds above the camp of the Israelites had disappeared. This is the meaning of 20,29: “the whole congregation saw that Aaron had died.” How could they all have seen it? They had not climbed Hor Hahar! They noticed that the cloud had disappeared and they realized that its presence had been due to Aaron’s merit. Up until that time the encampment of the Israelites had not been visible to the other nations at all. Rabbi Avohu said that instead of reading the word ויראו, “they saw,” it could be read וַיֵרָאוּ with the vowels tzeyre and kametz, and the meaning would be: “they had become visible.” Tanchuma also writes in that vein, i.e. the Jewish people now looked like a woman whose head-covering had been removed.
יג. הַכִּסּוּי שֶׁל הָראשׁ מֵבִיא לִידֵי יִרְאָה.
13. Covering the head brings one to fear of G-d.

is from a book by Rebbe Nachman of Breslov composed around 1810....by then head-covering had become a normal Jewish thing (for men).

Added by: Zahavit Shalev