Parshas Ki Setzei
“The garment of a man should not be on a woman and a man should not wear the clothing of a woman!” (Devarim 22:5)
It is a negative commandment that women may not wear the clothing of men and about this it says “The garment of a man should not be on a woman!”. It is likewise a negative commandment that men may not wear the clothing of women and about this it says “And a man should not wear the clothing of a woman!”.
Amongst the roots of this commandment are to distance our holy nation from anything remotely connected to immorality, and even from any possible thing which might contain a slight weakness regarding immorality. We see that Chazal said that Hashem hates immorality. This means that because Hashem loves us so much he distanced us from immorality which is a very disgusting thing and persuades a person’s mind to move from the good way and the correct thoughts towards bad ways and thoughts which are only nonsense. There is no doubt if men and women would have the same clothing they would be constantly intermingled and this would lead to the land being filled with immorality. They also said that another reason for this commandment is in order to distance us from anything remotely connected to idol-worship as idol-worshippers dress like this.
The prohibition for men is not only related to clothing. It applies to any way if self-adornment which is only for women. Examples of this are removing the white hairs from the black hairs on one’s head or beard and one who dyes his hairs in the way that women do.
This prohibition applies in all places and at all times.