What you can and can't wear

(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.

(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."

(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).

(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.