I guarantee you that if you start a conversation like any of these you’ve already lost before you’ve started:
- What were you thinking wearing something like that
- You look like a (fill in your pejorative) in that (article of clothing)
- That makeup makes you look like a (clown, floozy, hooker)
I mean, how do you respond if someone starts a conversation with an attack? I daresay most would get defensive. It gets made worse when the person presenting this says something like you should know better than to… along with the attack.
I was fifty five when I bought my first makeup. I devised a plan because I felt embarrassed and awkward. I realized that I could go to a local supermarket with a self checkout and buy whatever I wanted, and if I went later at night then it would be unlikely for anyone I knew to see me.
So one night after I had dinner with some guy friends I went by, bought some mascara, lipstick and foundation and retreated with my spoils.
Over the next year I slowly accumulated a small wardrobe of female clothing as I spend more and more time living as Rachel.
When I started at fifty five I didn’t know better than. I didn’t know who to ask for advice. What advice to trust. What products women use for what purposes. What that vast array of underclothing is for, and what kind of clothing appealed to me, for, um, me.
Take eyeliner, a fairly common makeup item. Eyeliner can be liquid, which is relatively hard to apply, a pencil, a gel pencil, a gel pot with a small brush, applied with a brush using an eyeshadow color or a specific eyeliner color, or one of these new fangled felt tipped marker things that are like the liquid eyeliner but not as tricky. How many kinds is that? That’s just what I’m aware of now after five years and I wouldn’t make any bets that I know them all.
That list for eyeliners can be repeated for lipsticks (liquid, stick, glosses, dyes….), foundations at different weights liquid and try, dry, gel and stick eyeshadows, and it just goes on and on and on.
If you visit Target there is something like three full aisles of drugstore makeup.
So for anyone to reproach a newly minted transwomen and say anything like “you should know” is just so far beyond reasonable as to be a joke. I’m not sure I’ve absorbed the names of all the basic kinds of shoes and purses yet.
What is a good approach? Something more like this:
I notice you really care a lot about your appearance and I love your choice of colors! Those are really nice shoes too.
Would you be open to my helping you with picking out clothes? I know it was really tough back when I was young learning what the right things to wear are.
You get the idea. Something that makes the person feel valued, and puts them in control. Something that doesn’t directly say anything about the current clothing being inappropriate. Let them ask. They will if you gain their trust and don’t reward them by hurting them when they ask.