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Kippah, Tallit, T'fillin
Kippah

As Chaldean astrologers told Rav Naḥman bar Yitzḥak’s mother: Your son will be a thief. She did not allow him to uncover his head. She said to her son: Cover your head so that the fear of Heaven will be upon you, and pray for Divine mercy. He did not know why she said this to him. One day he was sitting and studying beneath a palm tree that did not belong to him, and the cloak fell off of his head. He lifted his eyes and saw the palm tree. He was overcome by impulse and he climbed up and detached a bunch of dates with his teeth. Apparently, he had an inborn inclination to steal, but was able to overcome that inclination with proper education and prayer.

One who walks in an arrogant manner indicates a lack of regard for the glory and honor of God that is surrounding him, and thereby chases God from that place, as it were. The Gemara relates: Rav Huna, son of Rav Yehoshua, would not walk four cubits with an uncovered head. He said: The Divine Presence is above my head, and I must act respectfully.

In Talmudic times, the practice of wearing a headcovering was reserved for men of great stature. In later generations, though, it became the accepted custom for all Jewish men to wear a kippah at all times, and especially during prayer. As with all Jewish customs, once they become a universally accepted Jewish practice, they become halachically obligatory.
The Vilna Gaon said one can make a bracha without a kippah, since wearing a kippah is only an midot chassidut ("exemplary attribute"). Recently, there has been an effort to suppress earlier sources that practiced this leniency, including erasing lenient responsa from newly published books.
According to Rabbi Isaac Klein, a Conservative Jew ought to cover his head when in the synagogue, at prayer or sacred study, when engaging in a ritual act, and when eating. In the mid-19th century, Reformers led by Rabbi Isaac Wise completely rejected the kippot after an altercation in which Rabbi Wise's kippah was knocked off his head.

There is still debate about whether or not wearing a Kippah is Halachic law or simply a custom. Many Sephardic Jews wear a kippah only when praying and eating.
Blessing for wearing a kippah

בְּרוּכָה אַתְּ יָהּ אֱלֹקֵינוּ רוּחַ הָעוֹלָם תּוֹדָה שֶׁאַתְּ מַזְכִּירָה לִי שֶׁאַתְּ אִתִּי תָּמִיד

Brukhah at Yah, eloheynu ruach ha'olam, todah she'at mazkirah li she'at iti tamid.

Blessed are You, spirit of the Universe,
Thank you for reminding me that you are with me always.

Rabbi Malka Packer

Tallit
[The tzitzit will remind one of all the commandments] because the numerical value of the letters of the word tzitzit is six hundred, and there are eight threads and five knots in the fringes, so that you have six hundred and thirteen [which is also the number of the commandments of the Torah].

Rashi on Numbers 15:39
(לז) וַיֹּ֥אמֶר יי אֶל־מֹשֶׁ֥ה לֵּאמֹֽר׃ (לח) דַּבֵּ֞ר אֶל־בְּנֵ֤י יִשְׂרָאֵל֙ וְאָמַרְתָּ֣ אֲלֵהֶ֔ם וְעָשׂ֨וּ לָהֶ֥ם צִיצִ֛ת עַל־כַּנְפֵ֥י בִגְדֵיהֶ֖ם לְדֹרֹתָ֑ם וְנָֽתְנ֛וּ עַל־צִיצִ֥ת הַכָּנָ֖ף פְּתִ֥יל תְּכֵֽלֶת׃ (לט) וְהָיָ֣ה לָכֶם֮ לְצִיצִת֒ וּרְאִיתֶ֣ם אֹת֗וֹ וּזְכַרְתֶּם֙ אֶת־כָּל־מִצְוֺ֣ת יי וַעֲשִׂיתֶ֖ם אֹתָ֑ם וְלֹֽא־תָתֻ֜רוּ אַחֲרֵ֤י לְבַבְכֶם֙ וְאַחֲרֵ֣י עֵֽינֵיכֶ֔ם אֲשֶׁר־אַתֶּ֥ם זֹנִ֖ים אַחֲרֵיהֶֽם׃ (מ) לְמַ֣עַן תִּזְכְּר֔וּ וַעֲשִׂיתֶ֖ם אֶת־כָּל־מִצְוֺתָ֑י וִהְיִיתֶ֥ם קְדֹשִׁ֖ים לֵֽאלֹקֵיכֶֽם׃ (מא) אֲנִ֞י יי אֱלֹֽקֵיכֶ֗ם אֲשֶׁ֨ר הוֹצֵ֤אתִי אֶתְכֶם֙ מֵאֶ֣רֶץ מִצְרַ֔יִם לִהְי֥וֹת לָכֶ֖ם לֵאלֹקִ֑ים אֲנִ֖י יי אֱלֹקֵיכֶֽם׃ (פ)

(37) The LORD said to Moses as follows: (38) Speak to the Israelite people and instruct them to make for themselves fringes on the corners of their garments throughout the ages; let them attach a cord of blue to the fringe at each corner. (39) That shall be your fringe; look at it and recall all the commandments of the LORD and observe them, so that you do not follow your heart and eyes in your desire. (40) Thus you shall be reminded to observe all My commandments and to be holy to your God. (41) I the LORD am your God, who brought you out of the land of Egypt to be your God: I, the LORD your God.

The Torah says tzitzit (fringes) rather than tallit (garment or shawl). This is because the garments already existed! The commandment was about the addition of the ritual fringes. The style of dress in Judaism's early days was a wrap of rectangular garments. Over the centuries styles changed, and in many parts of the Jewish world, this commandment and ritual was faced with extinction. The Rabbis of the Talmud (4th - 6th centuries CE) decided to make it a special duty for us to go out of our way to continue wearing four-cornered garments in order to obligate ourselves in this mitzvah. They instituted two different garments for this purpose:

1. The tallit katan (the small tallit, often referred to as the tzitzit or arba kanfot). It is a small rectangular garment with a neck hole in the center and the requisite ritual fringes on the corners. It is worn by some Jews under their regular clothing all day every day.

2. The tallit gadol (the large tallit, often simply referred to as the “tallit”). The tallit is essentially a large rectangular piece of cloth with a ritual knotted woolen fringe added to each of its four corners. It is worn as a shawl, generally only in Synagogue during the morning worship services.

The classic material for a tallit is pure wool. The options are almost endless, though, with so many colors and color combinations to choose from.

According to some interpretations of Jewish law, wool is the only kosher option.

Tallitot are also very popular in acrylic and other synthetic materials. Other modern tallitot can be made from cotton and even pure raw silk.

The Talmud (b. Menachot 40-43 and y. Berakhot 3:3 [6b]; see also Sifrei 115) records that the opinion of the majority of rabbis was that women were obligated to wear tzitzit to the same extent that men were. The Talmud relates that one second-century sage, Rabbi Judah, used to “attach blue-dyed (fringes) to the aprons of the women of his household.” (b. Menachot 43a). Only one second-century rabbi, Rabbi Shimon, was listed as exempting women from the commandment of tzitzit.
Medieval rabbis generally adopted Rabbi Shimon’s position. Most ruled, though, that women were allowed to wear a garment with tzitzit if they wished. Some medieval authorities ruled that women who wore tzitzit could recite the blessing. Others disagreed. By late medieval and early modern times many rabbis actively opposed women wearing tzitzit. For example, Rabbi Jacob b. Moses Moellin (Maharil; Germany, c. 1360-1427) provides us with evidence that some women in his days still wore tzitzit but he writes:
Even though I have seen women wearing four-cornered garments with fringes, and still today there is one woman in our neighborhood, it seems astonishing to me and is arrogant of them. They are fools.
In the last few decades liberal Jewish writers, even some from Orthodox circles, have advocated for Jewish women to again observe the commandment of tzitzit, basing themselves on the early rabbinic texts.
Blessing for Putting on a Tallit

Blessed are You, Adonai our God, Ruler of the universe, who has sanctified us with Your commandments and commanded us to wrap oneself in fringes.

T'Fillin
(ז) מַצּוֹת֙ יֵֽאָכֵ֔ל אֵ֖ת שִׁבְעַ֣ת הַיָּמִ֑ים וְלֹֽא־יֵרָאֶ֨ה לְךָ֜ חָמֵ֗ץ וְלֹֽא־יֵרָאֶ֥ה לְךָ֛ שְׂאֹ֖ר בְּכָל־גְּבֻלֶֽךָ׃ (ח) וְהִגַּדְתָּ֣ לְבִנְךָ֔ בַּיּ֥וֹם הַה֖וּא לֵאמֹ֑ר בַּעֲב֣וּר זֶ֗ה עָשָׂ֤ה יי לִ֔י בְּצֵאתִ֖י מִמִּצְרָֽיִם׃ (ט) וְהָיָה֩ לְךָ֨ לְא֜וֹת עַל־יָדְךָ֗ וּלְזִכָּרוֹן֙ בֵּ֣ין עֵינֶ֔יךָ לְמַ֗עַן תִּהְיֶ֛ה תּוֹרַ֥ת יי בְּפִ֑יךָ כִּ֚י בְּיָ֣ד חֲזָקָ֔ה הוֹצִֽאֲךָ֥ יי מִמִּצְרָֽיִם׃ (י) וְשָׁמַרְתָּ֛ אֶת־הַחֻקָּ֥ה הַזֹּ֖את לְמוֹעֲדָ֑הּ מִיָּמִ֖ים יָמִֽימָה׃ (ס)

(7) Throughout the seven days unleavened bread shall be eaten; no leavened bread shall be found with you, and no leaven shall be found in all your territory. (8) And you shall explain to your son on that day, ‘It is because of what the LORD did for me when I went free from Egypt.’ (9) “And this shall serve you as a sign on your hand and as a reminder on your forehead—in order that the Teaching of the LORD may be in your mouth—that with a mighty hand the LORD freed you from Egypt. (10) You shall keep this institution at its set time from year to year.

(יד) וְהָיָ֞ה כִּֽי־יִשְׁאָלְךָ֥ בִנְךָ֛ מָחָ֖ר לֵאמֹ֣ר מַה־זֹּ֑את וְאָמַרְתָּ֣ אֵלָ֔יו בְּחֹ֣זֶק יָ֗ד הוֹצִיאָ֧נוּ יי מִמִּצְרַ֖יִם מִבֵּ֥ית עֲבָדִֽים׃ (טו) וַיְהִ֗י כִּֽי־הִקְשָׁ֣ה פַרְעֹה֮ לְשַׁלְּחֵנוּ֒ וַיַּהֲרֹ֨ג יי כָּל־בְּכוֹר֙ בְּאֶ֣רֶץ מִצְרַ֔יִם מִבְּכֹ֥ר אָדָ֖ם וְעַד־בְּכ֣וֹר בְּהֵמָ֑ה עַל־כֵּן֩ אֲנִ֨י זֹבֵ֜חַ לַֽיי כָּל־פֶּ֤טֶר רֶ֙חֶם֙ הַזְּכָרִ֔ים וְכָל־בְּכ֥וֹר בָּנַ֖י אֶפְדֶּֽה׃ (טז) וְהָיָ֤ה לְאוֹת֙ עַל־יָ֣דְכָ֔ה וּלְטוֹטָפֹ֖ת בֵּ֣ין עֵינֶ֑יךָ כִּ֚י בְּחֹ֣זֶק יָ֔ד הוֹצִיאָ֥נוּ יי מִמִּצְרָֽיִם׃ (ס)

(14) And when, in time to come, your son asks you, saying, ‘What does this mean?’ you shall say to him, ‘It was with a mighty hand that the LORD brought us out from Egypt, the house of bondage. (15) When Pharaoh stubbornly refused to let us go, the LORD slew every first-born in the land of Egypt, the first-born of both man and beast. Therefore I sacrifice to the LORD every first male issue of the womb, but redeem every first-born among my sons.’ (16) “And so it shall be as a sign upon your hand and as a symbol on your forehead that with a mighty hand the LORD freed us from Egypt.”

(ד) שְׁמַ֖ע יִשְׂרָאֵ֑ל יי אֱלֹקֵ֖ינוּ יי ׀ אֶחָֽד׃ (ה) וְאָ֣הַבְתָּ֔ אֵ֖ת יי אֱלֹקֶ֑יךָ בְּכָל־לְבָבְךָ֥ וּבְכָל־נַפְשְׁךָ֖ וּבְכָל־מְאֹדֶֽךָ׃ (ו) וְהָי֞וּ הַדְּבָרִ֣ים הָאֵ֗לֶּה אֲשֶׁ֨ר אָנֹכִ֧י מְצַוְּךָ֛ הַיּ֖וֹם עַל־לְבָבֶֽךָ׃ (ז) וְשִׁנַּנְתָּ֣ם לְבָנֶ֔יךָ וְדִבַּרְתָּ֖ בָּ֑ם בְּשִׁבְתְּךָ֤ בְּבֵיתֶ֙ךָ֙ וּבְלֶכְתְּךָ֣ בַדֶּ֔רֶךְ וּֽבְשָׁכְבְּךָ֖ וּבְקוּמֶֽךָ׃ (ח) וּקְשַׁרְתָּ֥ם לְא֖וֹת עַל־יָדֶ֑ךָ וְהָי֥וּ לְטֹטָפֹ֖ת בֵּ֥ין עֵינֶֽיךָ׃ (ט) וּכְתַבְתָּ֛ם עַל־מְזוּזֹ֥ת בֵּיתֶ֖ךָ וּבִשְׁעָרֶֽיךָ׃ (ס)

(4) Hear, O Israel! The LORD is our God, the LORD alone. (5) You shall love the LORD your God with all your heart and with all your soul and with all your might. (6) Take to heart these instructions with which I charge you this day. (7) Impress them upon your children. Recite them when you stay at home and when you are away, when you lie down and when you get up. (8) Bind them as a sign on your hand and let them serve as a symbol on your forehead; (9) inscribe them on the doorposts of your house and on your gates.

(יז) וְחָרָ֨ה אַף־יי בָּכֶ֗ם וְעָצַ֤ר אֶת־הַשָּׁמַ֙יִם֙ וְלֹֽא־יִהְיֶ֣ה מָטָ֔ר וְהָ֣אֲדָמָ֔ה לֹ֥א תִתֵּ֖ן אֶת־יְבוּלָ֑הּ וַאֲבַדְתֶּ֣ם מְהֵרָ֗ה מֵעַל֙ הָאָ֣רֶץ הַטֹּבָ֔ה אֲשֶׁ֥ר יי נֹתֵ֥ן לָכֶֽם׃ (יח) וְשַׂמְתֶּם֙ אֶת־דְּבָרַ֣י אֵ֔לֶּה עַל־לְבַבְכֶ֖ם וְעַֽל־נַפְשְׁכֶ֑ם וּקְשַׁרְתֶּ֨ם אֹתָ֤ם לְאוֹת֙ עַל־יֶדְכֶ֔ם וְהָי֥וּ לְטוֹטָפֹ֖ת בֵּ֥ין עֵינֵיכֶֽם׃ (יט) וְלִמַּדְתֶּ֥ם אֹתָ֛ם אֶת־בְּנֵיכֶ֖ם לְדַבֵּ֣ר בָּ֑ם בְּשִׁבְתְּךָ֤ בְּבֵיתֶ֙ךָ֙ וּבְלֶכְתְּךָ֣ בַדֶּ֔רֶךְ וּֽבְשָׁכְבְּךָ֖ וּבְקוּמֶֽךָ׃ (כ) וּכְתַבְתָּ֛ם עַל־מְזוּז֥וֹת בֵּיתֶ֖ךָ וּבִשְׁעָרֶֽיךָ׃ (כא) לְמַ֨עַן יִרְבּ֤וּ יְמֵיכֶם֙ וִימֵ֣י בְנֵיכֶ֔ם עַ֚ל הָֽאֲדָמָ֔ה אֲשֶׁ֨ר נִשְׁבַּ֧ע יי לַאֲבֹתֵיכֶ֖ם לָתֵ֣ת לָהֶ֑ם כִּימֵ֥י הַשָּׁמַ֖יִם עַל־הָאָֽרֶץ׃ (ס)

(17) For the LORD’s anger will flare up against you, and God will shut up the skies so that there will be no rain and the ground will not yield its produce; and you will soon perish from the good land that the LORD is assigning to you. (18) Therefore impress these My words upon your very heart: bind them as a sign on your hand and let them serve as a symbol on your forehead, (19) and teach them to your children—reciting them when you stay at home and when you are away, when you lie down and when you get up; (20) and inscribe them on the doorposts of your house and on your gates— (21) to the end that you and your children may endure, in the land that the LORD swore to your fathers to assign to them, as long as there is a heaven over the earth.

The text that is inserted inside the two boxes of Tefillin is hand-written by a scribe, and consists of the four sets of biblical verses in which Tefillin are commanded.

. . . as it was taught in a baraita: Michal, daughter of Kushi, King Saul, would don phylacteries, and the Sages did not protest against her behavior, as she was permitted to do so. And similarly, Jonah’s wife would undertake the Festival pilgrimage and the Sages did not protest against her practice.

Blessing for Putting On T'fillin
After placing the Tefillin on the left arm, before tightening the strap, the following blessing is recited:
Blessed are you, Lord our God, Ruler of the Universe, who sanctified us with God’s commandments and commanded us to place the tefillin.
The head tefillin is placed with the front at the hairline (or where that hairline used to be).
Blessed are you, Lord our God, Ruler of the Universe, who sanctified us with God’s commandments and commanded us regarding the mitzvah of tefillin.
Bring the straps around to the front with the shiny black side (the “front” side) facing out.
Blessed is the name of the Glory of God’s Kingdom forever.
Finally, the letters of one of God’s names, Shaddai (שׁדי) shin (שׁ), dalet (ד), yod (י) — are “written” across the hand using the tefillin straps. The strap of the arm tefillin is wrapped around the upper knuckle of the middle finger, once, and twice on the lower knuckle, with the second wrap extending across three fingers (see below). This makes the dalet and yod.

As the strap is wrapped around the middle finger, the following verse from the Book of Hosea is recited:
V’arashtikh li b’tzedek u’v’mishpat u’v’khesed u’v’rakhamim
V’arashtikh li b’emunah v’yadaht et adonai
Kadesh li kol b’khor pehtehr kal rekhem bivnei yisrael ba’adam u’vabhemah li hu.
I betroth you to me forever. I betroth you to me in righteousness, justice, lovingkindness, and mercy. I betroth you to me in faithfulness — and you shall know God.
The strap is wrapped again, diagonally, crossing the entire hand, except the thumb (see above) to form the second leg of the shin. Finally, the strap is wrapped once more around the middle of the hand, forming the middle leg of the shin.
Some Questions to Consider
In what ways does Judaism obligate or bind us? What does it mean to be bound to something?

How does what you wear express your identity as a Jewish person? How does what you wear express your identity as part of the Jewish people?

How can what we wear be symbols of relationships or ideas that are bigger than the symbols themselves?

When we are bound by Judaism to participate in a particular ritual, what freedom do we have to bring our own meaning to it?