Yeah I'd suggest that you come on over to the ftm subforum. Several people there are more transmasculine than male. We won't bite.
I'd agree with the earrings (I think *one* earring is more easy to wear as male). Yeah yeah males can have long hair and earrings and so on, but if you are trying to pass you have to think of if the thing you are wearing adds or subtracts to your look of the feminine and you have to lose the stuff that makes you look feminine. You might decide that it doesn't at all matter or you like X better than being read as male. But you are asking.
The haircut thing. You do not really want to cut it off, for some reason really really short gets read as butch. Not anything wrong with that mind you, but doesn't sound like the kind of look you want.
There's info on haircuts here (too bad but I lost a really cool link for haircuts with REAL haircuts instead of drawings). I don't go to a barber yet, but I came out to my hair stylist who is very supportive.
http://www.ftmguide.org/haircuts.htmlI never passed pre-T. But might be a bit due to age, I think that a person your age will sometimes pass but at a much younger age. If you can look across the street and tell what gender you think someone else is , well everyone is doing this. NOt to say they are necessarily right.
BTW, a lot of transmasculine people do not want to be told they are pretty women anymore than a mtf wants to hear "DUDE!"
--Jay