This is from this past weeks Torah club reading from FFOZ book #5. I believe this is very well put.
Cross-Dressing
Deuteronomy 22:5
A man is not to wear garments ordinarily worn by a woman, nor is a woman to wear garments ordinarily worn by a man. This is prohibition on cross-dressing, and it appears in the traditional enumeration of the 613 in a positive and negative form.
It is forbidden for a woman to put on men's garments. (N39)
It is forbidden for a man to put on women's garments. (N40)
The Torah says that cross-dressing is an 'abomination' to the LORD. For this reason, observant Torah communities tend to gravitate toward more traditional, modest dress, typically shunning the androgynous norms of today's society. It is for this reason also that most traditionalist communities discourage women from wearing the customary tallit (prayer shawl). For more than 2,000 years, the tallit has been regarded as a man's garment.
The prohibition on cross-dressing may shed light upon a difficult passage of Pauline material. In 1 Corinthians 11, Paul warns men not to wear head coverings6 in the manner of a woman's head covering. Though this has often been mistaken as a prohibition on a man wearing any head covering (e.g., the kippah), it is better understood as an admonishment against cross-dressers in the Corinthian congregation. Tebbitt points out that the Deuteronomy 22 passage has a direct bearing on the Corinthian passage, particularly 1 Corinthians 11:14-15.7
Does not even nature itself teach you that if a man has long hair, it is a dishonor to him, but if a woman has long hair it is a glory to her? For her long hair has been given to her for a covering. (1 Corinthians 11:14-15)
Tebbitt indicates that the word translated here as "nature," can have the sense of "culture" (i.e., the 'nature of things'). The culture that the Gentile disciples in Corinth had adopted was nothing other than the norms of the Torah itself, i.e., the Torah culture of Paul's day. In that culture, long hair, along with adorning, braiding and primping were typically feminine characteristics.8 Tebbitt's theory finds support in the Talmud, where we learn that the Sages of Paul's day
forbade men from primping their hair like women based on Deuteronomy 22:5.
The Sages agree with Rabbi Eliezer. A man who picks out white hairs from black ones is guilty.. .for it is said, "nor shall a man put on a woman's clothing." (b.Shabbat 94b quoting Deuteronomy 22:5)
In developing the Deuteronomy 22:5 reading of 1 Corinthians 11:14-15, Tebbitt goes on to speculate about the obscure statement that a woman's long hair is "a glory to her." In other words, a woman's hair, when it is worn long (i.e., in a feminine manner), is the appropriate expression of her femininity. At least long hair was the feminine cultural expression in Paul's day. He further suggests that the statement that a woman's hair "has been given to her for a covering" is probably meant to be understood in light of Deuteronomy 22:5. The word translated "covering" is the Greek word peribolaion, and it is used in the LXX to denote clothing or a garment in general. In fact, it is only used one other time in the whole of the Apostolic Scriptures, and it there it is translated as "garment."9 Thus, the statement may be read as "her long hair is given to her for a garment." Reading the apostle's admonition this way, we see that he is categorizing a woman's long hair as not only proper for her, but as a gender-specific garment. Regardless of the day or culture one lives in, this means that men should endeavor to look like men, and women should endeavor to look like women.
Cross-Dressing
Deuteronomy 22:5
A man is not to wear garments ordinarily worn by a woman, nor is a woman to wear garments ordinarily worn by a man. This is prohibition on cross-dressing, and it appears in the traditional enumeration of the 613 in a positive and negative form.
It is forbidden for a woman to put on men's garments. (N39)
It is forbidden for a man to put on women's garments. (N40)
The Torah says that cross-dressing is an 'abomination' to the LORD. For this reason, observant Torah communities tend to gravitate toward more traditional, modest dress, typically shunning the androgynous norms of today's society. It is for this reason also that most traditionalist communities discourage women from wearing the customary tallit (prayer shawl). For more than 2,000 years, the tallit has been regarded as a man's garment.
The prohibition on cross-dressing may shed light upon a difficult passage of Pauline material. In 1 Corinthians 11, Paul warns men not to wear head coverings6 in the manner of a woman's head covering. Though this has often been mistaken as a prohibition on a man wearing any head covering (e.g., the kippah), it is better understood as an admonishment against cross-dressers in the Corinthian congregation. Tebbitt points out that the Deuteronomy 22 passage has a direct bearing on the Corinthian passage, particularly 1 Corinthians 11:14-15.7
Does not even nature itself teach you that if a man has long hair, it is a dishonor to him, but if a woman has long hair it is a glory to her? For her long hair has been given to her for a covering. (1 Corinthians 11:14-15)
Tebbitt indicates that the word translated here as "nature," can have the sense of "culture" (i.e., the 'nature of things'). The culture that the Gentile disciples in Corinth had adopted was nothing other than the norms of the Torah itself, i.e., the Torah culture of Paul's day. In that culture, long hair, along with adorning, braiding and primping were typically feminine characteristics.8 Tebbitt's theory finds support in the Talmud, where we learn that the Sages of Paul's day
forbade men from primping their hair like women based on Deuteronomy 22:5.
The Sages agree with Rabbi Eliezer. A man who picks out white hairs from black ones is guilty.. .for it is said, "nor shall a man put on a woman's clothing." (b.Shabbat 94b quoting Deuteronomy 22:5)
In developing the Deuteronomy 22:5 reading of 1 Corinthians 11:14-15, Tebbitt goes on to speculate about the obscure statement that a woman's long hair is "a glory to her." In other words, a woman's hair, when it is worn long (i.e., in a feminine manner), is the appropriate expression of her femininity. At least long hair was the feminine cultural expression in Paul's day. He further suggests that the statement that a woman's hair "has been given to her for a covering" is probably meant to be understood in light of Deuteronomy 22:5. The word translated "covering" is the Greek word peribolaion, and it is used in the LXX to denote clothing or a garment in general. In fact, it is only used one other time in the whole of the Apostolic Scriptures, and it there it is translated as "garment."9 Thus, the statement may be read as "her long hair is given to her for a garment." Reading the apostle's admonition this way, we see that he is categorizing a woman's long hair as not only proper for her, but as a gender-specific garment. Regardless of the day or culture one lives in, this means that men should endeavor to look like men, and women should endeavor to look like women.