כלי גבר

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(ה) לֹא־יִהְיֶ֤ה כְלִי־גֶ֙בֶר֙ עַל־אִשָּׁ֔ה וְלֹא־יִלְבַּ֥שׁ גֶּ֖בֶר שִׂמְלַ֣ת אִשָּׁ֑ה כִּ֧י תוֹעֲבַ֛ת יְהוָ֥ה אֱלֹהֶ֖יךָ כָּל־עֹ֥שֵׂה אֵֽלֶּה׃ (פ)

(5) A woman must not put on man’s apparel, nor shall a man wear woman’s clothing; for whoever does these things is abhorrent to the LORD your God.

Cross dressing is a "negative" commandment, meaning we can not do it because it can cause someone to make a disgrace in front of hashem

(ה) לא יהיה כלי גבר על אשה. שתהא דומה לאיש כדי שתלך בין האנשים, שאין זו אלא לשם ניאוף:

(5) לא יהיה כלי גבר על אשה THE APPAREL OF A MAN SHALL NOT BE ON A WOMAN — so that she look like a man, in order to consort with men, for this can only be for the purpose of adultery (unchastity) (cf. Sifrei Devarim 226:1; Nazir 59a).

Connection to 10 דברות: If a women dresses like a man in a way that would make her look unrecognizable, a women might come to think she is a man, which can cause her to violate the commandment of לא תנאך, adulterous actions, which is a מצוה לא תעשה בין אדם לחברו

(ה) ולא ילבש גבר שמלת אשה. לילך ולישב בין הנשים דבר אחר שלא ישיר שער הערוה ושער של בית השחי:

(5) ולא ילבש גבר שמלת אשה NEITHER SHALL A MAN PUT ON A WOMAN’S GARMENT in order to go and stay unnoticed amongst women. Another explanation of the second part of the text is: it implies that a man should not remove the hair of the genitals and the hair beneath the arm-pit (Nazir 59a).

Part of cross dressing for a man is not removing hair unnecessarily, unless it becomes really uncomfortable according to the Shiur below

(ה) כי תועבת. לא אסרה תורה אלא לבוש המביא לידי תועבה:

(5) כי תועבת FOR [ALL THAT DO SO ARE] AN ABOMINATION [UNTO THE LORD THY GOD] — This implies that the Torah forbids only the wearing of a garb that leads to abomination (unchastity) (cf. Sifrei Devarim 226:1).

This law helps us avoid committing an unnecessary sin such as adultery.

(ה) לא יהיה כלי גבר על אשה - ללכת בין האנשים ולזנות.

(5) לא יהיה כלי גבר על אשה, in order to walk among males and seduce them.

we also see here a reference of violating לא תנאף-adultery

(א) לא יהיה כלי גבר על אשה. (נזיר כט) וכי מה בא הכתוב ללמדנו? [אם] שלא תלבש אשה כלים לבנים, ואיש לא יתכסה בגדי צבעונים, (ת"ל) [הרי כבר נאמר] "תועבה", דבר הבא לידי תועבה! [אלא] זה כללו של דבר - שלא תלבש אשה מה שהאיש לובש, ותלך לבין האנשים; והאיש לא יתקשט בתכשיטי נשים, וילך לבין הנשים.

(1) (Devarim 22:5) "A man's vestment shall not be upon a woman": What does Scripture come to teach us? If that she should not wear colored clothing, is it not written (Ibid.) "for the abomination, etc."? And this is not an abomination. It means, rather, that a woman should not wear what a man wears and go among the men (for licentious purposes), and a man should not wear colored clothing and go among the women.

Similar to what the Rashbam says that a women should not dress like a man because she may come to seduce. Sifrei adds that a man should not wear colored clothing and be around many women, while a woman should not wear men's items such as weapons and be around many men

(ח) וְאֶת־בָּנָ֖יו תַּקְרִ֑יב וְהִלְבַּשְׁתָּ֖ם כֻּתֳּנֹֽת׃ (ט) וְחָגַרְתָּ֩ אֹתָ֨ם אַבְנֵ֜ט אַהֲרֹ֣ן וּבָנָ֗יו וְחָבַשְׁתָּ֤ לָהֶם֙ מִגְבָּעֹ֔ת וְהָיְתָ֥ה לָהֶ֛ם כְּהֻנָּ֖ה לְחֻקַּ֣ת עוֹלָ֑ם וּמִלֵּאתָ֥ יַֽד־אַהֲרֹ֖ן וְיַד־בָּנָֽיו׃

(8) Then bring his sons forward; clothe them with tunics (9) and wind turbans upon them. And gird both Aaron and his sons with sashes. And so they shall have priesthood as their right for all time. You shall then ordain Aaron and his sons.

In these Pesookim, Hashem is instructing Moshe to clothe Aharon and his sons with the special clothing reserved for Kohanim. We learn from here that the way a person dresses is meant to distinguish between different classifications that society makes and the roles that we play. Here, the Kohanim have special clothing which they sanctify by performing actions in the Beit Hamikdash for a hashem. Cross dressing can distract us from our purpose in this life-use Torah as a guide to make our lives more holy and meaningful

(א) שלא תלבש אשה עדי איש - שלא ילבשו הנשים מלבושי האנשים ולא יזדינו בזינם, ועל זה נאמר (דברים כב ה) לא יהיה כלי גבר על אשה. ותרגם אונקלוס לא יהא תקון זין דגבר על אתתא (עי' נזיר נט א). ומן הדומה כי מפני כן פירש הכתוב בכלי זין, לפי שהם הכלים המיחדים לגמרי לאנשים, שאין דרך אשה בעולם לצאת בכלי זין, אבל הוא הדין שאסור להם מדאוריתא לצאת במלבושים שדרך האנשים באותו המקום להשתמש בהם, כגון שתשים בראשה מצנפת או שאר כלים המיחדים לאיש (עי''ש בתרגום יונתן בן עוזיאל).

(1) That a woman should not wear the adornments of a man: That women should not wear the clothing of men and not arm themselves with their weapons. And about this it states (Deuteronomy 22:5), "There shall not be the vessel of a man upon a woman." And Onkelos translated [it], "There shall not be a weapon of a man upon a woman" (see Nazir 59a). And that which is similar [is also prohibited]; since this is the reason that [Onkelos] explained Scripture as regarding weapons - because they are vessels that are completely unique to men, as it is not the way of a woman in the world to go out with weapons. But the same is true, that it is forbidden from the Torah, for them to go out with clothes that it is the custom of the men of that place to use - for example, that she should place a turban on her head or other vessels that are unique to a man (see Targum Jonathan on Deuteronomy 22:5).

G-d created objects specifically for men (EX-weapons) and women (EX-skirts). Therefore, a man should not get pleasure from that which belongs to a woman and vise versa. These thoughts can cause a violation of לא תחמד-not desiring what does not belong to you

(ה) לָא יִהְיֶה גּוּלְיַין דְּצִיצִית וּתְפִילִין דְּהִינוּן תִּקּוּנֵי גְבַר עַל אִיתָּא וְלָא יְסַפֵּר גְּבַר בֵּי שֵׁיחַיַא וְעִרְיְיתֵיהּ וּבֵי אַנְפּוֹי לְאִיתְחֲמָאָה הֵיךְ נְשָׁא אֲרוּם מְרַחֵק קֳדָם יְיָ אֱלָהָכוֹן הוּא כָּל דְּעָבִיד אִלֵּין

(5) Neither fringed robes nor tephillin which are the ornaments of a man shall be upon a woman; neither shall a man shave himself so as to appear like a woman; for every one who doeth so is an abomination before the Lord thy God.

Targum teaches us that a man must be careful when shaving because he should avoid making himself appear like a women. He also provides examples of what a woman should not wear

(א) שלא ילבש איש מלבושי אשה - שלא ילבשו האנשים מלבושי הנשים, ועל זה נאמר (דברים כב ה) ולא ילבש גבר שמלת אשה.

(1) That a man should not wear the clothes of a woman: That men should not wear the clothes of women, and about this it states (Deuteronomy 22:5), "and a man should not wear the garment of a woman."

We can also learn from here that a man shall not have the desire to wear women's clothing and a women shall not have the desire to wear man's clothing. Thoughts of cross dressing can cause a person to violate the commandment of לא תחמד-do not covet what is not yours

איכא דאמרי אמר ר' חייא בר אבא אמר ר' יוחנן המעביר בית השחי ובית הערוה לוקה משום (דברים כב, ה) לא ילבש גבר שמלת אשה מיתיבי העברת שיער אינה מדברי תורה אלא מדברי סופרים הוא דאמר כי האי תנא דתניא המעביר בית השחי ובית הערוה הרי זה עובר משום לא ילבש גבר שמלת אשה ותנא קמא האי לא ילבש גבר מאי דריש ביה מיבעי ליה לכדתניא (דברים כב, ה) לא יהיה כלי גבר על אשה מאי תלמוד לומר אם שלא ילבש איש שמלת אשה ואשה שמלת איש הרי כבר נאמר תועבה היא ואין כאן תועבה אלא שלא ילבש איש שמלת אשה וישב בין הנשים ואשה שמלת איש ותשב בין האנשים רבי אליעזר בן יעקב אומר מנין שלא תצא אשה בכלי זיין למלחמה ת"ל לא יהיה כלי גבר על אשה ולא ילבש גבר שמלת אשה שלא יתקן איש בתיקוני אשה אמר רב נחמן בנזיר מותר ולית הילכתא כוותיה אמרו ליה רבנן לר"ש בר אבא חזינא ליה לרבי יוחנן דלית ליה אמר להון מחמת זקנה נשרו ההוא דאיתחייב נגידא קמיה דרבי אמי. איגלאי בית השחי חזייה דלא מגלח אמר להון רבי אמי שיבקוה דין מן חבריא הוא בעא מיניה רב מרבי חייא מהו לגלח אמר ליה אסור אמר ליה והא קא גדל א"ל בר פחתי זמן יש לו כל זמן שהוא גדל נושר בעא מיניה רב מרבי חייא מהו לחוך אמר ליה אסור בבגדו מהו א"ל מותר איכא דאמרי בעא מיניה בתפלה בבגדו מאי א"ל אסור ולית הילכתא כוותיה:

Some say a different version of this statement: Rabbi Ḥiyya bar Abba said that Rabbi Yoḥanan said: A man who removes the hair of the armpit or the pubic hair is flogged, due to the prohibition: “A man shall not put on a woman’s garment” (Deuteronomy 22:5). The Gemara raises an objection from a baraita: The removal of hair is not prohibited by Torah law but by rabbinic law. How then does Rabbi Yoḥanan say that he is flogged, which by definition is a punishment for individuals who have transgressed a Torah law? The Gemara answers: It was he who said this halakha in accordance with the opinion of that tanna, as it is taught in a baraita: A man who removes the hair of the armpit or the pubic hair violates the prohibition of: “A man shall not put on a woman’s garment.” The Gemara asks: And what does the first tanna, who holds that the prohibition is by rabbinic law, learn from this verse: “A man shall not put on a woman’s garment”? The Gemara answers: He requires it for that which is taught in the baraita, where it states: “A woman shall not wear that which pertains to a man, and a man shall not put on a woman’s garment, for whoever does these things is an abomination to the Lord your God” (Deuteronomy 22:5). What is the meaning when the verse states this? If it teaches only that a man may not put on a woman’s garment, and a woman may not wear a man’s garment, it is already stated in explanation of this prohibition that “it is an abomination to the Lord your God,” and there is no abomination here in the mere act of wearing a garment. Rather, it means that a man may not wear a woman’s garment and thereby go and sit among the women; and a woman may not wear a man’s garment and sit among the men. Rabbi Eliezer ben Ya’akov says: From where is it derived that a woman may not go out with weapons to war? The verse states: “A woman shall not wear that which pertains to a man, and a man shall not put on a woman’s garment,” which indicates that a man may not adorn himself with the cosmetics and ornaments of a woman, and similarly a woman may not go out with weapons to war, as those are for the use of males. Rabbi Yoḥanan’s ruling follows this opinion. § Rav Naḥman said: For a nazirite, it is permitted to shave armpit hair. The Gemara comments: And the halakha is not in accordance with his opinion. The Gemara reports that the Sages said to Rabbi Shimon bar Abba: We have observed that Rabbi Yoḥanan does not have armpit hairs, despite his own ruling that it is prohibited to shave them. He said to them: They fell out due to old age. The Gemara relates: There was a certain person who committed a transgression and was found liable to receive lashes before Rabbi Ami. When they removed his clothes to flog him, his armpit was exposed, and Rabbi Ami saw that he had not shaved his armpit hair. Rabbi Ami said to his attendants: Leave him; this is one of those who are meticulous in observance of mitzvot. We can see this is so, as he is particular about prohibitions that ordinary people do not observe. Rav raised a dilemma before Rabbi Ḥiyya: What is the halakha with regard to shaving armpit hair? He said to him: It is prohibited. Rav said to him: But it grows and is uncomfortable. Rabbi Ḥiyya said to him: Son of nobles [bar paḥtei], this hair has a limited time. Whenever a hair grows too long it falls out, and therefore there is no concern that one’s armpit hair will become too long. Rav raised another dilemma before Rabbi Ḥiyya: What is the halakha with regard to rubbing armpit hair and thereby removing it manually? Rabbi Ḥiyya said to him: It is prohibited. Rav continued to ask: What is the halakha with regard to rubbing armpit hair indirectly with one’s garment? Rabbi Ḥiyya said to him: It is permitted. Some say that this was not Rav’s question; rather, he raised the following dilemma before him: What is the halakha with regard to rubbing the armpit with one’s garment during prayer? Rabbi Ḥiyya said to him: It is prohibited. The Gemara comments: And the halakha is not in accordance with his opinion in this case.

Rabbi Nachman says a Nazir is actually allowed to shave armpit hair, however this Gemara brings down an example of a Nazir who did not shave his armpit hair and was actually saved from receiving lashes for a sin he committed

According to Rab Hiyya, if a man's armpit hair grows very long it will eventually fall out so he should not worry about it being uncomfortable. Rav asks him a question about rubbing the hair (with a garment) and he responds that its permitted, but not during prayer

שלא תעדה אישה עדי איש, שנאמר "לא יהיה כלי גבר על אישה" (דברים כב,ה).

39. That a woman should not wear a man's clothes as it says "the garment of a man should not be on a woman” (Devarim 22:5)

There are certain objects that hashem created specifically for a man and specifically for a woman. For example, a woman should not carry a gun just like a man should not wear a skirt

שלא יעדה איש עדי אישה, שנאמר "ולא ילבש גבר שמלת אישה" (דברים כב,ה), מפני שזה היה מנהג עובדי עבודה זרה וכן מפורש בספרי עבודתה.

40. A man shall not wear woman's clothes like it says " a man should not wear the garments of a woman” (Devarim 22:5) because this was the custom those who served idol worship and this is also explained in the Sifri the way it was served.

One of the 10 commandments is not worshipping other gods (ע"ז). If one gets into the habit of cross dressing, he or she might start to act like someone who is an idol worshipper and may come to violate this איסור

Contemporary Source-YuTorah.org

http://www.yutorah.org/sidebar/lecture.cfm/863710/rabbi-isaac-rice/contemporary-issues-in-cross-dressing-part-2/#

  • Rashba-A man can remove body hair below the neck if it becomes uncomfortable. You can be lenient if you deal with a law on a Derabanan level.
  • Taz-you can put on clothing of other gender if it is cold out. We are lenient even with a Deoraytah if there is a great need for it. EX-A man can use a feminine umbrella if its raining and a woman can put ski pants if she's going skiing
  • If a man has a gray hair, he can not remove it. There is a machloket if you can color discolored patches of hair. There is an opinion that says it is okay if it causes discomfort.
  • If a piece of Jewelry has a masculine design, a man is permitted to wear it. Ex-ring, wedding band
  • A man can use feminine products such as a women's shampoo or makeup to cover a blemish
  • Nail polish is problematic for men
  • A women should not carry a weapon because it is considered something that men wear. Ex-story with Yael. She takes a tent pin to kill Sisera, instead of using a weapon. However, if a women is carrying a weapon to protect her family, it is ok or if enemies enter the land, a women can carry a weapon and even DRESS IN MEN'S CLOTHING to avoid being assaulted
  • If no men are around, a woman can wear men's clothing like sweatpants. She can also wear pants designed for women like exercise pants if needed
  • Why is this Misva after hashavat Avedah? If an object is in a muddy area, it is hard for a women to go get it in a skirt. Similarly, the Misvah of Shiluach Haken is right after, to show that if a women needs to climb a tree to get the bird, she is permitted to wear pants because it will protect her
  • Case-many girls were wearing mini skirts and the school administration tried to convince them to dress more צנוע. It was not working, so they asked Hacham Ovadia what to do and he said that in this case it would be okay for the girls to wear pants because it will cover their bodies more.