(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.
... “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.
(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.
(1) 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).
(3) 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).
לֹא תַּעֲדֶה אִשָּׁה עֲדִי הָאִישׁ כְּגוֹן שֶׁתָּשִׂים בְּרֹאשָׁהּ מִצְנֶפֶת אוֹ כּוֹבַע אוֹ תִּלְבַּשׁ שִׁרְיוֹן וְכַיּוֹצֵא בּוֹ אוֹ שֶׁתְּגַלֵּחַ רֹאשָׁהּ כְּאִישׁ. וְלֹא יַעֲדֶה אִישׁ עֲדִי אִשָּׁה כְּגוֹן שֶׁיִּלְבַּשׁ בִּגְדֵי צִבְעוֹנִין וַחֲלִי זָהָב בְּמָקוֹם שֶׁאֵין לוֹבְשִׁין אוֹתָן הַכֵּלִים וְאֵין מְשִׂימִים אוֹתוֹ הַחֲלִי אֶלָּא נָשִׁים הַכּל כְּמִנְהַג הַמְּדִינָה...
A women shall not adorn herself with man's adornment, such as a mitre, or a helmet, or a coat of armor, and the like, or cut the hair of her head man-fashion; neither shall a man adorn himself with the adornment of a women, for instance to wear loud-colored garments or golden ornaments in a territory where such clothes are not in style for men to wear or where such ornaments are not put on by any save women, all depending on the custom of the land...
That a woman should not wear the adornments of a man: ...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).
It is from the roots of the commandment [that it is] to distance our holy nation from matters of sexual immorality and any matter and any angle whatsoever that contains a stumbling block towards it - as the matter that they, may their memory be blessed, said metaphorically (Sanhedrin 106a) that our God hates promiscuity. [This] means to say, that in His love for us, He distanced us from promiscuity, which is an exceedingly ugly thing, [and which] takes the heart of a man and pushes it off from the good path and from desirable thoughts, to a bad path and thoughts of stupidity. And there is no doubt that if the clothes of men and women were the same, they would constantly mix - these with those - 'and the world would be filled with promiscuity.' And they also said in explaining this commandment that it is to distance all matters of idolatry, as the way of the worshipers of idolatry was with this.
A woman may not clothe herself in men's clothing, e.g. put on her head a mitre or helment, or wear armor, and so on (Rama: from that which men wear in accordance with the local custom (Tur)) or shave her head like a man. A man may not clothe himself in the clothes of a women, e.g. wear colored clothing or golden ornaments in a place where only women wear those things...
לא תלבש אשה וכו' דברי רבינו בדין זה סתומים דמשמע דבכל ענין אסור ואינו כן אלא יש היתר בשני דברים. האחד שאין איסור אפי' בדבר שהוא נוי וקשוט אלא א"כ באשה הלובשת בגדי איש להתדמות לאיש ואיש הלובש בגדי אשה להתדמות לאשה אבל אם לובשין כדי להגן מפני החמה ביה"ח וביה"ג מפני הגשמים אין שם איסור ו... והשני דאף להתדמות אין איסור אלא בדברים שהם עשוים לנוי ולקשוט וכדאיתא בספרי בפסוק ולא יהיה כלי גבר וכי מה בא הכתוב ללמדנו יכול שלא תלבש אשה כלים לבנים והאיש לא יתכסה צבעונין ת"ל תועבה דבר המביא לידי תועבה זהו כללו של דבר שלא תלבש אשה מה שהאיש לובש ותלך לבין האנשים והאיש לא יתקשט בתכשיטי נשים וילך לבין הנשים
The law is lenient in two respects, First of all, no prohibition applies, even against wearing something that makes one more attractive, unless one does so to resemble the opposite sex. Clothing worn as protection against the summer sun or winter rain presents no problem.
Second of all, even is a man intends to resemble a women, no prohibition applies unless in doing so he thereby beautifies himself. As the Sifri states "...a man should not adorn himself with female adornments."
Therefore, male garments worn by women when they go to the market and sit in shops violate no prohibition. They are made only as clothing to cover the body, not for beautification or adornment. Moreover, women wear them only as protection from exposure to the elements, not to resemble men.
QUESTION: During the winter, are women allowed to wear trousers under their clothing as protection against the cold? ANSWER: One may rely upon the view of Bah and Taz that even an outright male garment is permissible if worn as protection against the cold. Shakh forbade only a man's so dressing up that one cannot tell he is a man. His entire focus is on the person, not his garb, such that if a man wears only one female garment, and does not intend to resemble the opposite sex, he violates no prohibition. Surely, trousers beneath a woman's clothing, or even over them, are permissible, since the woman will ultimately be recognized as such by her other clothing, and since she is only wearing this garment as protection from the cold. Tosafot's pronouncement that a man may gaze into a mirror to avoid hurting himself applies fully here. Yet, even without my answer, there is still no problem, for after investigation, I have become aware that women's trousers can be distinguished from men's, being that the two are different. Thus, there are two points in your favor: 1) There is no intention to resemble men, and 2) they are different from a man's. Both here and in Poland, even pious, modest women have long practiced this, without a complaint being heard. A greater problem, however, is the new phenomenon of women wearing men's hats and suits. Although the feminine version of these items differs slightly from the male version, they are apparently worn by some women for the sole purpose of resembling men. These would seem to be forbidden, and I have previously made an uproar about this, demanding that their forbidden status be publicized. Unfortunately, many trespass in this regard, as well as by wearing non-Jewish fashions. May God have mercy on us!
QUESTION: Is there any prohibition against women wearing women's slacks, which are like trousers, but are never worn by men, and are distinguishable by such factors as color?
ANSWER: This question does not require elaborate investigation, for an outright prohibition is involved. Besides, ostentatious clothing such as this is produced, a priori, for sin, and is associated with promiscuity. Even if they are not classed as "male articles," wearing them still constitutes an "abominable act." The truth is that they are real, male articles, and even if they are a bit different, they are still labeled trousers. Likewise, Avnei Tzedek wrote regarding men's hats and suits that a woman's purpose in wearing either can only be to resemble a man. Even if the female version of these is a bit different from the male version, their labels will still apply, hence they should be forbidden. From what age does the prohibition apply? Surely, once a girl reaches educable age, she must be taught about this like any other mitzvah. Even before then, however, we are forbidden to supply her with forbidden fruits by our own hand,'!' as the Poskim explain, especially as regards an act which due to its sexually corruptive nature, may lead the public to sin as well.
May a woman wear such trousers at home? When visitors are there, trousers are obviously as forbidden as when she is in public. Yet, even when she is home, alone, and no one can see her, she still violates K'li Gever. As proof, a man is forbidden to remove his pubic and underarm hair. Is she allowed to wear trousers to go skiing, when skiing without them is difficult, and when if she falls, they actually provide an advantage? This seems to depend on a debate among the Poskim regarding whether a woman is allowed to wear male garb as protection against the elements. On close scrutiny, however. it appears that even to wear one such garment is forbidden according to all opinions. Even Shakh is lenient only where exposure to the elements is not a matter of choice. Yet who would allow her to wear male garb to go skiing? Better she should stay home and not dress this way ... especially as a Torah prohibition is involved.