Tips on Passing?

[RyGuy]

and sorry if we all sound really critical or are bombarding you with information, we just like to be helpful around here and each of us knows a fair bit about passing

[Hadrian]

I'm sorry but all the jewelry does NOT read female to me. It is in no way girly in my opinion. Maybe it's just the culture where I grew up, I don't know, but the jewelry has nothing to do with it. He just looks like a rocker type dude to me. Definitely the second picture is far more male to me though, the first, I think it's the hair for sure there.

[Kerberos]

For the best haircut that is masculine and will be seen as male, go to a good barber shop.

Barbers cut usually only guys haircuts and specialize in the "cleaning up" that has been posted for a good tip. I go to the barbers every 3 weeks at the most in order to keep my hair lines in check as I have thick hair. Google barbershop haircuts and you should be able to find some standard cuts for your friend to pick.

[insideontheoutside]

I think the issue with the "masculine haircut" is that it makes most guys who have even remote feminine features look like a butch lesbian. That's just my opinion but the large majority I've seen I think butch before I think male. Having less hair just seems to accentuate facial structure, the fact that you don't shave, etc. Some guys may end up looking male - but like a 13 year old instead of their actual age.

I think the hair thing should definitely be experimented with to find what makes you look more male without accentuating other things or making you look like a young boy.

As for jewelry, it's true a lot of guys don't wear it (maybe a ring or two or something simple) but if it's something he really likes he shouldn't necessarily give it all up. Just experiment with that as well.

[Andy]

The main thing is to keep working on it, keep shifting things little by little till it works. I am pre-op, no T, and I pass ALL THE TIME, just by taking the tips I have read on here! You will get lots of good advice, just have to tweak it, gain confidence, and wham! In the past week, I have been called man, sir (multiple times), guy, Mister, gentleman, and "little boy"! LOL (that last one's pretty funny, seeing's how old I am!)

Patience, practice, trial-and-error! He'll get there!! Good luck and hang in there. 

[Cowboi]

I think the issue with the "masculine haircut" is that it makes most guys who have even remote feminine features look like a butch lesbian. That's just my opinion but the large majority I've seen I think butch before I think male. Having less hair just seems to accentuate facial structure, the fact that you don't shave, etc. Some guys may end up looking male - but like a 13 year old instead of their actual age.

I agree with this actually. Sometimes it can work against a person but you never really know till you do it and see. I would say definitely get his side burns cut shorter. Men don't grow out the longer sideburns that fall in front of your ears like women do, if it's short on the sides the hair tends to stop at the top of the ear for side burns maybe a bit lower (think if he had glasses on it would touch the glasses going over his ear but wouldn't really hang down below the glasses, I know this because I wear glasses and use that as a check point myself lol).

I do not agree with the jewelry thing, and that is mostly because I am familiar with the rock/punk/goth kind of look, it is very common for men to wear lots of jewelry with that style so long as the jewelry itself is masculine (you know not tiny and girly, flowery, etc) which does not seem to be an issue for him anyhow.

Sadly his issue with first look is face, face shape. He may experiment with holding his jaw different ways to create more of a square jaw effect. Like for me, if I place my bottom front teeth directly in front of my top front teeth when I have my mouth closed just that difference made a huge impact in how I was taken when I was a teenager. Basically, just the opposite of how you put your teeth when you close your mouth naturally. If he can do that, even for just that first minute when he is introduced to someone it may help. Obviously it would be uncomfortable to do it constantly. Also I can't tell how he holds his shoulders but there are different ways to stand/sit/and hold yourself that will make his shoulders look bigger and more squared. Do you know when you see little guys walking around and they have their shoulders hunched up all high and walk with their arms straight swinging slightly, pull themselves up as tall as they can stand and they always look like some kind of jackass who is pissed off and trying to look "tough" and "big"? Practice with that kind of stance. Obviously he doesn't want to appear like he's pissed all the time but it's a starting point to give you kind of an idea of what I mean by "holding his shoulders" differently. If he can look larger in the shoulders or more broad basically that will help.

And definitely, experiment with binding because in the pictures he does not look like he's that large but if he's already binding we wouldn't be able to tell anyhow. Do you know how he currently binds? If he is using a binder has he tried adjusting his chest to lay in different ways? I've had a lot of guys tell me to just push them downward and flat, but when I push mine up and then pull them to the side (kind of towards my armpits) it actually looks better on me, more like I have a bit of a muscled chest with some small pecks.