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About 10 years ago, I went through gender reassignment (assigned male at birth) and started living as a female. I had all my documents, including my passport changed to reflect this.

Recently, I made the decision to "detransition" in terms of my appearance, due to various reasons such as the social difficulties that trans people face (Risk of violence, discrimination when finding work, etc).

This was really just a change in my appearance - I cut my hair short and stopped wearing make-up and generally just wear jeans and t-shirt. I still consider myself to be female, I just don't look it.

I now have the problem that the gender on my passport does not match how most people see me. My photo is also out of date because my hair is now short. Obviously I need to at least update the photo, but am I likely to have problems at the border if my gender doesn't appear to match even though my appearance does?

(I did get questioned at the border in Ukraine because I hadn't had the chance to change my passport, but due to the language barrier it was hard to tell if they were more concerned about the appearance differences or my gender. They did eventually let me through after asking to see some old photographs of me.)

I plan on travelling to Florida soon and would like to go back to Ukraine next year. I'd rather not change the gender on my passport (it might be quite difficult to do anyway).

I'm wondering if I can try to mitigate problems by trying to appear more feminine when I cross the border? Or are trans people just always going to have problems in places like Ukraine?

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    Sorry to hear you are encountering these problems when traveling. When entering the US, you may be asked to face a facial recognition apparatus, so that will very likely work in your favor. All the best to you :)
    – user79729
    Commented Sep 3, 2018 at 14:31
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    Another way is, if someone is questioning your passport just by looking at it, you can politely request the biometrics check (fingerprints, facial recognition, signature).
    – user79729
    Commented Sep 4, 2018 at 15:47
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    Have you been to the US before on that passport? If so they should have your fingerprints on record, that will make life easier at that border.
    – JenniP
    Commented Sep 7, 2018 at 14:19
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    You probably will face problems from many countries. Does not mean they will not ultimate allow entry, however it will not be smooth.
    – Augustine of Hippo
    Commented Sep 7, 2018 at 15:31

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You may face trouble if you try to travel to Egypt.

This Hebrew news story from 2018-09-05 tells of a transgender woman, with feminine appearance (see picture in article) but listed as male in her passport, who was refused entry into Egypt.

My partial translation:

After a night of driving we have passed the Israeli side of the border. On the Egyptian side we were delayed for almost three hours, with my passport passed between something like 10 border officers debating what to do with it. Eventually, after we were not communicated with, left to dry and wait, we were notified that my entry into Egypt is refused, because my passport's gender section says "male" - and that all I have to do is change it to female. It didn't help explaining that there's nothing invalid with the passport - for them it was not valid.

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