I would suggest going to the barber and telling him you want your face to look more masculine and see what he suggests. Tell him you want a cut that will highlight/create a more squared off jaw. I honestly believe that is where passing comes into play the most. "Round face" natal males still have a different shape than round faced natal females in my opinion.
My hair stylist has known me for 15 years. I have always had a haircut that was a male cut, but on the androgynous end of the spectrum. I presented as female at work, so I went as masculine as I could with my hair cut, still keeping in mind needing to be read (or rather as believable), as female. In my job I am meeting new people every day, so bonding quickly with people is necessary for my work. That is harder to do the further you are away from society's gender expression expectations. I was already wearing men's clothes, and of course no makeup or anything, so I couldn't go completely over the edge with hair. Anyway...
After I started got on T and living as male, we changed the cut to an obvious male cut that focused completely on creating a stronger jaw line.
Anyway, I am sure that there are men that go to the barber all the time requesting a cut that would make their face look more masculine. All guys want that kind of look (so, if they don't have it, they would seek it). I would maybe go with a style in mind, but let the barber tweak it to how it would look best. These folks have been looking at faces for eons. They know better than we do, IMHO. You can always change it next time if you don't like it.
