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Seudah Shlishit Trip to South
מצוות השמחה והחסד / תחפושת ואיסור לא ילבש
The Mitzvot of Joy and Kindness / Costumes and the Prohibition of Lo Yilbash
נהגו רבים ללבוש מסכות ולהתחפש בפורים, ואף שאין לכך מקור בדברי חז"ל, וגם בספרי האחרונים לא כתבו שצריך להתחפש, מכל מקום נאמרו הסברים שונים למנהג. הראשון, להרבות בשמחה, כי ההופעה המשונה מצחיקה ומשעשעת. ועוד, שעל ידי היציאה של האדם משגרת לבושו, הוא יכול להשתחרר ולשמוח ולגלות את אהבתו לחבריו. ועוד, שהלבושים החיצוניים השונים גורמים לפירוד, ועל ידי החלפת הלבושים, נופלות המחיצות ומתרבה האחדות. ועוד, שעל ידי התחפושת אנו נעשים מודעים עד כמה אנו מושפעים מהחיצוניות, ומתוך כך אפשר להתבונן בפנימיות שמתגלה בפורים. ועוד רמז בתחפושת, שגם כאשר ישראל נראים כלפי חוץ כגויים, בפנימיותם הם נשארים יהודים, כפי שהתברר בפורים.
Many people customarily wear masks and costumes on Purim. Even though there is no source for this in the writings of the Sages, and the Aḥaronim did not write that one must wear costumes, various reasons have been given for the custom. The first reason is that it increases our joy, as a person with an unusual appearance can be amusing and entertaining. Another reason is that when one departs from his normal attire, he is able to let loose, rejoice, and display his love for his friends. Another reason is that having different modes of dress causes disunity among the Jewish people, and changing our external appearances on Purim breaks down the barriers between us and increases unity. Another reason is that by wearing costumes, we become aware of the degree to which we are influenced by external elements, and as a result, we can focus more on the internal elements that are revealed on Purim. Finally, costumes allude to the fact that even when the Jews look like gentiles on the outside, they remain Jews deep down, as the Purim story made clear.
כתב מהר"י מינץ (תשובה טז), שנהגו בבתי גדולים וחסידים באשכנז, שהיו מתחפשים, וגברים לבשו בגדי נשים, ונשים בגדי גברים. וכתב שאין להרהר אחריהם, ובוודאי אין בזה חשש איסור, משום שכל איסור 'לא ילבש' הוא כאשר מחליפים את המלבושים למטרת ניאוף ופריצות, אבל כאשר המטרה לשמחה, אין איסור. וכתב הרמ"א (תרצו, ח), שכך המנהג.
Mahari Mintz writes that the custom in the homes of great and pious individuals in Germany was to dress up on Purim; men even wore women’s clothing and women wore men’s clothing (Responsa §16). He comments that one should not think poorly of them, since there is certainly no concern that this is prohibited. After all, the prohibition of lo yilbash (the prohibition against cross-dressing) refers only to wearing the clothing of the opposite gender for purpose of adultery and licentiousness. However, when this is done for the sake of rejoicing, it is not prohibited. Rema (696:8) writes that this is the accepted practice.
אולם לדעת פוסקים רבים, אסור לאיש להתחפש לאשה, ואסור לאשה להתחפש לאיש (ב"ח יו"ד קפב, ט"ז ד). וכן נכון לנהוג. ויש אומרים שאם החליף רק בגד אחד ומשאר בגדיו עדיין ניכר מינו, אין למחות בידו (פמ"ג).
Most poskim, however, maintain that a man may not dress up as a woman, and a woman may not dress up as a man (Baḥ YD 182; Taz YD 182:4). Based on this, many Aḥaronim write that one should censure those who wear the clothing of the opposite sex. This is the correct practice. Some maintain that if a person changes only one article of clothing, and that person’s sex remains recognizable based on the other garments, one should not denounce him (Pri Megadim).
המן מן התורה מנין (בראשית ג, יא) המן העץ
They also asked Rav Mattana: From where in the Torah can one find an allusion to the hanging of Haman? He replied: The verse states after Adam ate from the tree of knowledge: “Have you eaten of [hamin] the tree, about which I commanded you that you should not eat?” (Genesis 3:11). Hamin is spelled in the same manner as Haman: Heh, mem, nun.
אסתר מן התורה מנין (דברים לא, יח) ואנכי הסתר אסתיר מרדכי מן התורה מנין דכתיב (שמות ל, כג) מר דרור ומתרגמינן מירא דכיא:
They also asked Rav Mattana: From where in the Torah can one find an allusion to the events involving Esther? He replied to them that the verse states: “Then My anger shall be kindled against them on that day, and I will forsake them, and I will hide My face from them, and they shall be devoured, and many evils and troubles shall come upon them; so that they will say in that day: Have not these evils come upon us because our God is not among us? And I will hide [haster astir] My face on that day for all the evil which they shall have wrought, in that they are turned to other gods” (Deuteronomy 31:17–18). They also asked him: From where in the Torah can one find an allusion to the greatness bestowed upon Mordecai? He replied: As it is written with regard to the anointing oil in the Tabernacle: “And you shall also take the chief spices, of flowing myrrh [mor deror]” (Exodus 30:23); and we translate mor deror into Aramaic as: Mira dakhya, which resembles the name Mordecai.
וַתָּ֩סַר֩ בִּגְדֵ֨י אַלְמְנוּתָ֜הּ מֵֽעָלֶ֗יהָ וַתְּכַ֤ס בַּצָּעִיף֙ וַתִּתְעַלָּ֔ף וַתֵּ֙שֶׁב֙ בְּפֶ֣תַח עֵינַ֔יִם אֲשֶׁ֖ר עַל־דֶּ֣רֶךְ תִּמְנָ֑תָה כִּ֤י רָאֲתָה֙ כִּֽי־גָדַ֣ל שֵׁלָ֔ה וְהִ֕וא לֹֽא־נִתְּנָ֥ה ל֖וֹ לְאִשָּֽׁה׃
So she took off her widow’s garb, covered her face with a veil, and, wrapping herself up, sat down at the entrance to Enaim, which is on the road to Timnah; for she saw that Shelah was grown up, yet she had not been given to him as wife.
וַיִּרְאֶ֣הָ יְהוּדָ֔ה וַֽיַּחְשְׁבֶ֖הָ לְזוֹנָ֑ה כִּ֥י כִסְּתָ֖ה פָּנֶֽיהָ׃
When Judah saw her, he took her for a harlot; for she had covered her face.
וַתָּ֣קׇם וַתֵּ֔לֶךְ וַתָּ֥סַר צְעִיפָ֖הּ מֵעָלֶ֑יהָ וַתִּלְבַּ֖שׁ בִּגְדֵ֥י אַלְמְנוּתָֽהּ׃
Then she went on her way. She took off her veil and again put on her widow’s garb.
וַיְכַ֣ל מֹשֶׁ֔ה מִדַּבֵּ֖ר אִתָּ֑ם וַיִּתֵּ֥ן עַל־פָּנָ֖יו מַסְוֶֽה׃
And when Moses had finished speaking with them, he put a veil over his face.
וּבְבֹ֨א מֹשֶׁ֜ה לִפְנֵ֤י ה' לְדַבֵּ֣ר אִתּ֔וֹ יָסִ֥יר אֶת־הַמַּסְוֶ֖ה עַד־צֵאת֑וֹ וְיָצָ֗א וְדִבֶּר֙ אֶל־בְּנֵ֣י יִשְׂרָאֵ֔ל אֵ֖ת אֲשֶׁ֥ר יְצֻוֶּֽה׃
Whenever Moses went in before ה' to converse, he would leave the veil off until he came out; and when he came out and told the Israelites what he had been commanded,
וְרָא֤וּ בְנֵֽי־יִשְׂרָאֵל֙ אֶת־פְּנֵ֣י מֹשֶׁ֔ה כִּ֣י קָרַ֔ן ע֖וֹר פְּנֵ֣י מֹשֶׁ֑ה וְהֵשִׁ֨יב מֹשֶׁ֤ה אֶת־הַמַּסְוֶה֙ עַל־פָּנָ֔יו עַד־בֹּא֖וֹ לְדַבֵּ֥ר אִתּֽוֹ׃ {ס}
the Israelites would see how radiant the skin of Moses’ face was. Moses would then put the veil back over his face until he went in to speak with God.
Rabbi Norman Cohen:
Purim’s masks may seem to conceal, if just for a moment, the chaos and pain of our present lives and enable us to escape this reality, but they may really offer us the chance to don serious masks of conscious determination to bring the light of the Divine into our world. Yes, God may not be mentioned in the entire book of Esther, and some have seen this as an intimation of the existence of sheer chaos in the world, where anarchy is at play. Yet, we must ask what lies beneath a story that intimates the absence of God and meaning, and the holiday of Purim, which is about frivolity and play.
Questions for Discussion:
1. How and when can dressing up allow us to reprieve from the stresses of life?
2. When in your life has changing your clothing been therapeutic?
3. How does Mordecai's story here offer an insight on why there is a tradition for dressing up during Purim?
4. Why do you think Mordecai, according to Midrash (Pirke D'rabbi Eliezer), has trouble transitioning from clothes of mourning to clothing of royalty? When have you made a stark transition from one style of clothing to another?

וַיְהִ֨י אֹמֵ֜ן אֶת־הֲדַסָּ֗ה הִ֤יא אֶסְתֵּר֙ בַּת־דֹּד֔וֹ כִּ֛י אֵ֥ין לָ֖הּ אָ֣ב וָאֵ֑ם וְהַנַּעֲרָ֤ה יְפַת־תֹּ֙אַר֙ וְטוֹבַ֣ת מַרְאֶ֔ה וּבְמ֤וֹת אָבִ֙יהָ֙ וְאִמָּ֔הּ לְקָחָ֧הּ מָרְדֳּכַ֛י ל֖וֹ לְבַֽת׃

And (Mordechai) brought up Hadassah, (Hadassah) is Esther, his uncle’s daughter; for she had neither father nor mother, and the maiden was of beautiful form and fair to look on; and when her father and mother were dead, Mordechai took her for his own daughter.

אסתר מן התורה מנין (דברים לא, יח) ואנכי הסתר אסתיר

Where is Esther indicated in the Torah?

In the verse,"And I will surely hide [astir] my face." (Devarim 31:18)