I heard somewhere that the prophet PBUH wore eyeliner (kohl) himself as well as have long hair, dyed it, etc, given the gender norms at the time. So, what’s the stance on wearing feminine clothing if it’s NOT for sexual pleasure, and is one’s identity in a society that allows/embraces such diversity (the west) without expressing negativity? Besides wearing silk or gold, which is okay for me to avoid, can I just wear perceived feminine clothing/wear eyeliner (kohl)? I do not feel sexual feelings regarding this. However, I definitely show signs of distress when not being able to express myself in this way, and I want my face to somehow appear feminine looking as well. I’ve even seen men wear things resembling skirts (kilts) and ear piercings in the west for example aren’t really considered ‘feminine’ anymore.

So, I am wondering if this is permissible given all of my circumstances.

by

The use of kohl for men is not prohibited, and so is the extension of hair, unless it is an imitation of women.
As for wearing women’s clothes and putting on women’s makeup and lipstick, for example, this is an imitation of women without any problem, and it is abhorrent in Shariah, and your love for this does not make it permissible.