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Some chassidic shirts are basically identical to women's dress shirts, save for the bust shape, i.e. they button right-over-left.

Would a female wearing the former be transgressing the prohibition on cross-dressing, due to the garment being manufactured and sold specifically for Jewish men?

Chassidic shirt

Warning: Female bust shape below! Hover to reveal.

Women's shirt

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    I've always wondered whether the reverse was true, if men wearing clothing made according to the chassidic buttoning style violated the same commandment. – Noach MiFrankfurt Aug 27 '14 at 18:42
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    @NoachmiFrankfurt How would that be? Is buttoning-direction a universal or a Jewish principle? If so, it hasn't always been. – Adám Aug 27 '14 at 18:58
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    @NBZ I haven't tried, but I'm told by friends who have that women's pants can also fit either gender. – MTL Aug 28 '14 at 19:28
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    Why is the picture of the women's shirt hidden in a spoiler? – Scimonster Jan 25 '15 at 18:27
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    @Adám - And how is that seeing your sister or mother wearing a shirt. – ezra Apr 16 '17 at 18:25
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Regarding the general rules about women wearing men's clothing, from Halachos for Monday, May 6, 2013 in this article:

1) A woman may not wear men's clothing, including men's pants and men's hats, as doing so is a biblical prohibition of "Lo Yihyeh Kli Gever Al Isha, a man's clothing shall not be on a woman" (Devarim 2:5.)

This prohibition extends to any action done by a woman to make her look like a man, including shaving in a masculine manner.(See Rashi ibid. and Shulchan Aruch Yoreh Deah Siman 182:5)

2) Some Poskim rule that the prohibition is only in place when done for the express purpose of looking like a man, but if wearing a man's garment for protection from the sun, rain or other elements it would be permitted.(Taz on Shulchan Aruch Yoreh Deah Siman182 S"K 4)

However, other Poskim are stringent, and it is best for a woman to avoid men's clothing at all costs. (Ruling of the Bach quoted in Taz ibid.)

Item 2, above, states a leniency, in general.

Regarding the specifics of the shirt that you mention, I have to locate another article that I saw that deals with the specifics of shirts and pants. (It may have been written by someone from OU.) It states a general rule that clothes that have become the norm to be worn by both genders such as jeans, slacks and shirts do not pose a violation of this halacha. Of course, it assumes that the clothing being worn meet tzniut standards.

I will try to edit this answer once I can locate that source.

Somewhat aside - women who exercise wear gym shorts and sweats. I am assuming that since this is the norm for exercising, there is no violation, but, perhaps, the leniency is restricted only to exercising and not, e.g., grocery shopping?

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    The Bach doesn't say that. The Bach was only saying to avoid cross-dressing for Purim. – Fred Dec 23 '14 at 1:34
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    Note that the article quoted SINGLES OUT PANTS AND HATS, which are uniquely tailored for men. While it's true that, as noted, the bust of a woman means the shirts are usually tailored differently, one may argue that the subtle difference isn't significant enough - since both genders wear shirts - to "ban" wearing a shirt "not tailored for a woman." – Isaac Kotlicky Jun 25 '15 at 14:34
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Shirts that are styled with the collars and cuffs as shown in the photograph are considerd masculine, in a style which was adaptd for women in the last century. Maybe that is what iscausing the question. Depending on which side the buttons are placed many people regard the shirt made for a man or a woman and some women's shirts also include,the side pleats. It makes for a modest and classic styled shirt when the collar is buttoned to the top and the sleeve's cuffs are buttoned at the wrist.

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    In other words, you're saying that it isn't a problem at all, as even if the shirt was actually made for women it would still be masculine enough for a man to wear? – Adám Oct 4 '17 at 11:27
  • As long as there are not side darts ( as for women's blouses) and the buttons are according to the tradition for men's shirts, the shirt style is according to the photograph then it would be masculne. Having read your question though, if the intention of the maker is that it is made for a woman, maybe that muddles the correctness. – gamliela Oct 4 '17 at 11:42
  • Well, the question was actually about women wearing men's shirts, not the other way around, but this is interesting as well. – Adám Oct 4 '17 at 11:44
  • I think I was just reflecting that this style of shirt is a masculine one. I have worn such shirts marketed for women because they are frequently made of cottn, long sleeved and when buttoned completely to the top serve as a very modest way of drewsing in summer when combined with a skirt. Later I thought of getting rid of these shirts because of the masculine styling. I'm still not sure about it for women. – gamliela Oct 4 '17 at 11:52
  • Maybe, once it becomes popular for orthodox women, the style ceases to be decidedly masculine? Just like maris ayin can possibly cease from parve ice cream, because everyone knows. Certainly, dress shirt+skirt is extremely popular among chassidic girls. – Adám Oct 4 '17 at 11:57
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women may not wear men's clothing. this question is assuming a particular shirt is women's clothing. If it were to be women's clothing then women could wear it but since the question is based on a false premise then these shirts would stay remain male clothing and no women may not wear them.

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