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Some chassidic shirts are basically identical to women's dress shirts, save for the bust shape, i.e. they botton 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 mi Frankfurt Aug 27 at 18:42
    
@NoachmiFrankfurt How would that be? Is buttoning-direction a universal or a Jewish principle? If so, it hasn't always been. –  NBZ Aug 27 at 18:58
    
@NBZ Is this a piece of clothing meant for men, or a piece of clothing meant for women? ....if it's meant for men, I would include it in the prohibition; if not, not. Why should it matter if it involves a feature that used to be only for women? [for example, would it be forbidden for a man to wear a woman's suit with pants? Those used to be only worn by men....but this one was made for women] ( no source no answer ) –  Shokhet Aug 28 at 3:22
    
@Shokhet "manufactured and sold specifically for Jewish men" –  NBZ Aug 28 at 13:22
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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. –  Shokhet Aug 28 at 19:28

1 Answer 1

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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