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A man may not wear clothes clearly meant for women, nor may a woman wear clothes clearly designed for men. As it says, “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” (Deuteronomy 22:5). There are two reasons for this prohibition. First, to prevent immodest behavior, which may lead to a rise in adultery and the weakening of the institution of the family. Second, so that we may preserve our unique identities. Clearly, it is forbidden to undergo sex reassignment surgery. Not only does that transgress the prohibition of cross-dressing, it transgresses the far more severe prohibition of sterilization (8:8 above).
