Sefer HaChinuch ספר החינוך

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.”

What is written concerning the previous commandment is from the roots of the commandment.

The laws of the commandment: That which they, may their memory be blessed, said (Makkot 20b) that the prohibition and lashes are not only for clothing, but the same is true about their grooming; as anyone who grooms himself with the adornments that are unique to women is obligated in [getting] lashes — for example, one who plucks out white hairs from among the black ones from his head or from his beard; and so [too] one who dyes his hair in the way that women dye theirs. And so did Onkelos translate, “and a man should not groom with the adornments of a woman.” And that which they, may their memory be blessed, said (see Mishneh Torah, Foreign Worship and Customs of the Nations 12:10) that a tumtum and an androginus (two categories of people the sex of which is in doubt) should, like a woman, not wrap their head; and should, like a man, not shave their head; and [that] if they do so they are not lashed. And so [too,] in every place, we give them the stringencies of men and of women; but if they transgressed, they are not lashed, because they [represent] a doubt. But if they transgressed a prohibition that a man and a woman are equal in, it is not necessary to say about this that they are lashed for it. And its other details are elucidated in Tractate Nazir [in the] chapter [entitled] Shnei Nizirim (Nazir 59a).

And this prohibition is practiced in every place and at all times by males. And one who transgresses this, and wears the clothes of women or grooms himself with the adornments of women — for example, he plucks out white hairs from among black ones or he dyes even one hair — is liable for lashes, from when he plucks it or dyes it.