Will I ever pass?

Your hair is very orange! (that's a good thing. Great colour )

Yes, I think you could pass. Can you fiddle around with how you style your hair within that haircut? Use product to switch it up?
Your face shape is androgynous IMO so I don't think you'd have major issues in that respect.

 

I think it's definitely possible. You'd need to change your hair, but your face isn't super distinctly feminine, so with the right hair/clothes people could totally read you as a guy.

 

Anyone can pass if they do the right thing. Your face is already fairly masculine (eyes & lips especially). With the right clothes & hair for sure, and definitely on T.

 

I don't agree with this : Genetics and the age play a major role.

Will you pass? I can't tell you.

Will you feel happier when you change your clothes, hair, name and the rest? Definitely, and there is the place where genetics and age can screw themselves!

But yeah... You seem to have good cards, but as I have said I can't tell you, I don't have a crystal ball, and I'm not sure I would want one.

 

Your face looks androgynous, if not male; the main thing is your hair. If you played around with different ways of styling it, that would help a lot.

 

I don't mean right away, I mean it's never impossible to ever pass, like a person could go on hormones, gain/lose a lot of weight, get plastic surgery, etc.

 

I won't put my hand on fire for something that it's just not 100% sure.

Plastic surgery? Well, if you can afford it, that is...

That's just me, I won't put my hand on fire, but people can do whatever they want, same as I do.

 

Id say you could

 

I definitely think so. I think the big thing is your hair. How it's parted right now it's a little feminine but I think with a little fading on the side and some cropping, you'd look damn good. Give this a shot: The Best Hairstyles for Round Faced Men. Frankly, you just look young. I know a lot of young cis guys who look a lot like you so don't feel bad about your face. If you need a closet look, I'd suggest getting a pixie cut or a beanie/hat you can wear over your hairline.

 

Yeah, you can pass. You do look rather feminine in that pic, but you also remind me a lot of one of my best friends in that pick, who is also a transmale and now passes quite well. A less "cute" and "feminine" haircut would probably go a long way to help you. Beyond that age and hormones are really all I would recommend.

But yeah, you'll probably look a bit younger than you really are (which sucks) but otherwise I think you can quite easily pass fine.