Men's and Women's Clothing
I was in a vintage clothing store and saw a great shirt that looked comfortable. I was about to buy it and the salesperson said, "Is this for you? You know, this is a woman's blouse." I was surprised, and then I thought about the appropriateness of me wearing women's clothes. What do you say, rabbi?
The Aish Rabbi Replies:
"Beged isha" is the Torah prohibition of men wearing women's clothing or vice versa, as is written: "Male garb shall not be on a woman, and a man shall not wear a feminine garment" (Deut. 22:5).
The Sefer HaChinuch (#542) explains that the purpose of this mitzvah is to help maintain a separation between the sexes. If men and women were to wear each other's clothing, they would eventually become intermingled and would fall into licentiousness.
The precise parameters of what constitutes "men's and women's clothing" depends on a given society's norms. For example, in Scotland it would be permitted for a man to wear a kilt (skirt), but not in other places. Earrings are another example: years ago, before they became popular with men, it was forbidden for a man to wear one; today that is changing.
This realm of Jewish law extends beyond clothing to other activities, such as dyeing one's hair to remove the gray. Again, it depends on local custom: If it is acceptable for men to do such a thing, then it is not considered a women-specific activity.
Further, it would be permitted for a man to wear one item of women's clothing for some functional reason -- e.g. he is stuck in the pouring rain and only has a woman's raincoat.
If you have a specific question, please write back.