Question: What does the Torah have to say about clothing for men and women? How similar can they be? Why should/shouldn’t there be any difference between them?

Answer: Thank you very much for your interesting question. We do not find in the Torah any commandments to wear specific clothing, other than the clothing that the Kohanim (priests) were commanded to wear when performing the service in the Temple. However, we are commanded to be holy, and exhorted to be modest. Other than that, the exact dress styles are pretty much left up to the tastes of the society in that generation, other than it is prohibited to dress in a way that is uniquely Gentile.

However, in societies such as ours where there are different clothing unique to men and women, it is prohibited by the Torah to “cross dress”, even if most of the garments you are wearing are that of your sex, and only one garment is that of the opposite sex. However, this does not apply to garments that are often unisex. In our society, there would be nothing wrong with a wife wearing a husbands sweater or sweat shirt.

This prohibition is stated in Devarim/ Deuteronomy 22:5, and the details are discussed in the Kitzur Shulchan Oruch/ Concise Code Of Jewish Law, ch. 171.

The Sefer Hachinuch (Mitzvah 542) explains that the reason why G-d forbade this is because “cross dressing” is often a prelude to immoral acts, and we must distance any such possibility from our Holy Nation as much as possible. However, it does apply in all cases, even in situations where it may not seem to you and I that it would lead to immorality.

Take care,
Rabbi Aaron Tendler