You guys are all looking great!! Some awesome progress on this thread

Trying- I agree that you pass better in the first photo. I think your hair being a bit messier helps you out, and you do have a prominent Adam's apple! It also might be that the part in the second photo shows off your hairline? I can't exactly pinpoint what says female to me...

Jossef- you've always passed to me! I think passing as male vs passing for your age is the struggle you face now. If you are very set on looking older, I would ditch the hat and try more conservative clothes. Think polos, dress shoes, button downs, khakis, etc. I don't think your glasses would look out of place if you dressed like this.
Blake- wow definite changes between your two photos! You look very similar to a young gay guy I know who's about 18. You are a handsome guy and T is only helping further that!
Zombie- you look great man! Some really prominent changes between your two photos. You have absolutely nothing to worry about; anyone who thinks you look soft is blind! Your glasses and facial hair really add to your masculinity. Congrats on a year on T and your weight loss!!