That sort of scruffy "rocker" hair works, I think. Lolol Queen
. I think it's sort of equal parts looking like you just woke up after a long night of partying and looking like you might not have bathed recently.
I did this
for a while. Which really just consisted of "comb your hair straight back and let dry and then let it do whatever the next day".
And "punk" styles where you look like you attacked a fan for shits and giggles. No hate, I luv dem punx.
For short hair, you really have to be explicit about wanting a male cut. It's "sharper" on the sides, with a more abrupt transition from short sides to longer top.
But when it comes to "passing", you really have to play to society's gender cues, unfortunately. It's also important, if you're going for a more masculine look, to call more attention to your feature that are naturally more masculine and away from the feminine ones.
If I can, it works best for me to have my hair back at the top, at least exposing forehead to hairline, and not much hair around the jaw area so as not to soften it.
Also, eyebrows. They are one of the things that does more than anything else when it comes to aesthetic traits. I've found for me, at least, when I had NO eyebrows, it actually looked more masculine than little stingy girly ones - because it brought perceived browline down to my eyesockets.
And "typically female" facial hair tends to actually do more 'harm' than good to trying to pass as male. Because guys tend to either go big or just shave it off - they don't have that "peach fuzz" - they have stubble.
BUT, I want to stress, there's no wrong way to be masculine or male.
My hair is pretty short right now, but I want to grow it again. Guessing it'll be four-five more months, just in time for school, I guess. I had my hair permed for a while, so it did need to get cut off because it was crispy. I just have to enjoy life being more Oscar Wilde than Gene Wilder, I guess. So I guess the lesson is, "don't fight your hair, it will do what it wants to do or fall out from chemical abuse".