Ki Seitzei - The Prohibition of Cross-Dressing

In Parshas Ki Seitzei we read of the prohibition of cross-dressing (Deuteronomy 22:5):

The vessels of a man shall not be on a woman, and a man shall not don a woman's garment; for whoever does these things is an abomination to Hashem your God.

In practical terms, this means that we may not wear garments associated with the opposite gender. Moreover, as understood by the Sages, the prohibition also forbids men from specific behaviors - such as shaving body hair or dyeing their hair - that are commonly associated with women, and the same rule applies to women.

Most sources explain that the reason for this prohibition is that it can lead to immoral behavior and also that such cross-dressing was associated with idolatry. However, many commentaries see a more fundamental issue here, as R' Avraham Ibn Ezra (d.1164) concludes his commentary on this verse:

... ה' יתעב מי שישנה מעשה ה'.

God abominates he who changes God's deeds.

Similarly, the Rekanti (kabbalistic commentary on the Torah by R' Menachem Rekanti, d.1305) writes:

פשטו ידוע, אמנם על דרך הקבלה יש לך לדעת כי הרמז הוא שלא ישנה סדרי בראשית וכו'

The simple meaning [of the prohibition] is well know, however, kabbalistically, you should know that the symbolism [of the prohibition] is that one should not change the structure of Creation....

The Toldos Yakov Yosef (R' Yakov Yosef of Polnoye, d.1794) explains that the basic idea underlying this prohibition is that every person must accept the role, i.e. the unique task that God has given him, and not attempt to challenge or change that role.

Every human being has unique spiritual capabilities which no other person can duplicate. Thus, every human being has a unique role to play in bring the world to its ultimate state of perfection. As the Sages teach us (Talmud, Sanhedrin 37a):

כל אחד ואחד חייב לומר בשבילי נברא העולם.

Every person is obligated to say, "The world was created for my sake!"

Every individual plays an essential role in the world, and we are obligated to recognize this. As each of us has a unique role in this world, there is no way to compare the circumstances of different individuals. Just as responsible parents need to work with each child as an individual, in order to enable that particular child to fully develop his own unique potential, as we are taught in Proverbs (22:6), "חנך לנער על פי דרכו" - "Educate the child according to his way," so too God directs the circumstances of our lives in order to provide us with the ideal circumstances in which to develop our own unique spiritual potential. Thus, each of us experiences different challenges in life, different spiritual affinities, different temptations to sin, and so on, for each of us has a different task to achieve.

As God's children, our role is to trust Him and to accept the role that He has given us and by doing so we relate to Him as children to a father. This is particularly important at this time of year, as we prepare for the day of judgment on Rosh Hashana. Our relationship with God has two basic levels, that of Father and child and that of King and servant. While both are always present, in many places in our prayers we express the hope that, when we come before God in judgement, the Father-son relationship should be dominant.

As many sources make clear, the primary factor that determines how God relates to us is how we view our relationship with Him. If we see God as a powerful king who imposes decrees on us which we have no choice but to obey, then we relate to Him as a servant to a King. But if we relate to God as a wise and loving father whose rules and demands are always purely for our benefit, then we relate to Him as a child to a Father.