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What does Judaism say about the appropriateness of men wearing women's clothes, and vise-versa?
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?
"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 possible example. Years ago, before they became popular with men, it was forbidden for a man to wear one; today that might be changing.
Unisex clothing would likewise generally be okay, with the exception of clothes or colors originally designated for one gender which then began to be produced for both, as that is viewed as a means of consciously undermining modest behavior and the separation of he sexes. An example of this are pants for women. (Note that apart from this, pants for women would be forbidden because the garment itself is not considered modest for women.)
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.
(For some sources see: Shulchan Aruch Y.D. 182, Tzitz Eliezer XI 62.)