My experience and approach have been a little different from some of the other women here. I started experimenting with my appearance indoors and then soon after went out fully en femme–but in a nearby city, not in my home area. This was really freeing and educational, since I could do it without having to worry about interacting with people who (at the time) I wasn’t out to. I expanded over time to going out in female mode locally, but only to queer-friendly venues, and since then it’s expanded to almost wherever–although I still seem to find excuses not to be in female mode at the local little grocery store and hardware, which are the kind of places where people know your name and your family. That will be something to get over in the near future.
I think things are made easier for me in some respects (and much harder in others) because I’m bi-gender–in my case, sometimes male and sometimes female–so I don’t always have to choose between the easy way out (going in male mode) and feeling like my authentic self. I’ve also had an easier time than a lot of people because I live in an area that’s (on the whole) unusually trans-positive and supportive–for instance, I go to the same Pride center where Taylor Small, who just got elected to the Vermont House of Representatives, works. The areas I visit (Boston, Montreal, Northampton, etc.) also tend to be “safe” locations for trans people. For people who are feeling extremely unsafe being themselves in public, I even wonder if it’s worth moving to a location like this. I’m sure I would have had a harder time if I lived in, say, some of the cities in the South or Midwest.
I pass sometimes and don’t pass sometimes: maybe I’m passing 10% of the time, maybe 90%–I honestly can’t be sure! While I would *love* to always know when I was passing (at least, I think I’d love to know), I’ve had to make my peace with the fact that I usually won’t be able to be sure–and moreover, there’s no need for me to be.
Another thing that helps me is that I have a lot of martial arts training, which makes me feel like if I were ever physically accosted by someone using anything less deadly than a gun, I’d probably be able to fend them off. I’ve never had to do anything like that, and don’t expect to! But knowing I can defend myself makes a huge difference to my feelings of safety. There are self-defense training classes (SPEAR training is especially good, of the ones I know) that could help with this if it’s a concern for anybody.
So over years of being out in public in female mode, as with Carly, the worst that has happened to me in person is being misgendered–and I can only think of a couple of times that’s happened. The only person who’s ever been rude and dismissive about my gender, honestly, has been a trans woman on a forum, who astonishingly tried to tell me that “bi-gender” wasn’t really a thing and that I was lying to myself and/or others. I was amazed that she did not hear that she was using the exact same nonsense arguments people use to dismiss binary trans women.
Anyway, I generally can’t tell whether I’m passing beautifully or if people are just behaving kindly and appropriately–and the thing I recently decided to try was just not caring. Unless someone’s going to actively try to harm me, it doesn’t matter whether I pass for them or not, and if I don’t, it doesn’t matter whether they like it or not. I’m used to being extremely vigilant, to trying to guess what people are thinking, to worry that I’ve made some choice that makes it harder for me to pass, all of which feels mentally and emotionally exhausting–yet when I make myself give that up and decide to just not care, suddenly my way is much easier, and things feel much better.
All that said, I’m not necessarily recommending that practice! I know that we all have our own unique situations, ways of coping, strengths, limitations, and environments. I have been finding, though, that for me, just not caring what other people think is a choice I’m able to make if I work at it and makes things much better for me.