At least at first. I’m most aware of this with trans women, I’ll leave trans men for someone else to talk about. Trans women never got to go through that awkward pubescent stage of dressing inappropriately and using makeup badly, being taught by mothers and older sisters about appropriate clothing, appropriate makeup, and just plain experience in a safe environment (or not so safe) to learn how to be first an adolescent girl and then a young women with ever growing confidence in her appearance.
Instead a trans women gets to start at some age from twenty to seventy where there’s much less room to look badly because all the natal females around you know what they are doing.
The problem? At once you have this person who needs help, is emotionally vulnerable, wants to get to live a lost life experience and can’t afford to look like a fool. Oy vey.
My wife had a particularly hard time with me. For awhile I was in denial because she was trying but she was also conflicted. After I went full time she was great. She made sure I didn’t go out the door looking like an idiot. It made a huge difference knowing that.
With the above in mind, and adding on that the person you’re dealing with is probably emotionally vulnerable, providing useful feedback becomes both essential but a real exercise in care.
Most people would say that if you need to give someone negative feedback it might better be given in a way that the person is guided to the conclusion or realization themselves. They might also suggest positive reinforcement before and after. Let me tell you about my doing it the wrong way. I had good intentions, I really did, and I was really careful in how I said it, I really was, but.
I was talking to a friend in the community and as I am mentioning above we get to try and relive our youth at a, ahem, more mature age and she was no exception. She was wearing a skirt that was considerably too short, not the first I had seen her in, so I thought I should say something. So I tried to do so in a kind way and she basically covered her ears and shut me out and walked away. To be fair, if I had done it perfectly the same thing might have happened.
A better approach might have been to complement her on something else, and perhaps influence her by telling her how I’ve done that and not even talk about what she was doing (only because I know her to be sensitive). Would that have worked? Maybe not too.
The truth is, until your friend is ready to accept that they need advice and help they won’t be likely to listen. I had a number of people beyond my wife telling me outright or using euphemisms to try to help me along. It really just took time and understanding. In the meantime I was fortunate enough to not make a total fool of myself. I just wore some skirts that were four inches too short like the friend I was trying to talk to. What, me the pot calling the kettle black? No, never…