Hey, guys, by popular request, I'm starting a topic on style advice for guys who prefer to have long hair. I have pretty stupidly long hair, and I'm really stubborn about cutting it, but I can still pass sometimes even though I'm pre-everything and not terribly consistent in my presentation anyway (I'm genderqueer/transmasculine). I'm by no means an expert, but here's what I know about making long hair look masculine. Also, sorry that all the pictures are in links; I didn't want to get in trouble for embedding pictures that totally aren't mine and that I didn't ask to use, even if it's for illustrative purposes. I hope this is helpful (and in the right place)!
When it comes to getting it cut, just have them cut it straight across if you have relatively straight hair (
http://www.edgrochowski.com/edphoto4.jpg), and it'll look like this when it gets disordered:
http://img233.imageshack.us/img233/8818/forjoelpg6.jpg. Layers are typically feminine, and they show up more with straight hair:
http://angelbrewhaha.files.wordpress.com/2009/01/layered-hair.jpg. If your hair is on the curlier end of things, no one will be able to tell if it's layered:
http://improbable.com/projects/hair/pre-2003/paravidino-hair-hi-res.jpg. Though a few guys in '80s metal bands pulled off bangs (
http://specials.rediff.com/movies/2007/mar/20sld5.jpg), it's pretty much not a good strategy for passing if the rest of your hair is long. One last thing is that higher testosterone levels can make the short, finer hairs at the hairline on the sides and back fall out to make a masculine hairline, so it would be pretty reasonable to buzz them off. (I tried really hard to find a picture of a guy with a ponytail with the wispy stuff buzzed off, but I couldn't find one. I swear I saw this on law enforcement guys in the city where I grew up.) If you want to keep the length but have less hair, consider an undercut. Here's a really extreme one:
http://p1.hotornot.com/bl/brands/NYNUEM/GJQGCPCTXVEJDHMNKVFG.jpg. And here's a more moderate one:
http://i11.tinypic.com/4u3i8w4.jpg.
Regarding caring for your hair in general, don't overthink it. I shampoo and condition my hair every other day and brush it maybe once a week, probably less. I think not brushing it often contributes significantly to passing, even though some folks might find that gross. Along with that, I haven't gotten a trim in 6 years and a real haircut in much longer, so I can rock the "my hair has reached its terminal length due to split ends" look, which I think is even more masculine than a straight-across cut:
http://i228.photobucket.com/albums/ee256/Isjungfrun/9k01nq.jpg. Also, dreads can be really masculine or at least not feminine, if you can pull it off. For everyday styling, try to leave it alone as much as possible. Don't bother using a comb to part it. Just let it go where it wants when you get out of the shower: bonus points if that's roughly in the middle, as a part that's too far to one side tends to look feminine. If you need to tie it back, keep the ponytail low, as in, just below or at the point where your hair stops growing on your neck. Pre-T, you might not have a very masculine hairline, so if you can, leaving it down or at least not pulled back as much as down should help hide that. If you leave it down (or if it's really, really long and in a ponytail), don't play with it!
Again, I'm not declaring myself king of long hair; I've got a lot to learn, too, but these are the things that work for me plus some stuff I've heard elsewhere. For what it's worth, my partner's a cis-guy with long hair, and from time to time he gets mistaken for a woman, so even if you're on T, you might still not pass 100%, and that might just be part of the long hair deal for you, so don't take it as a personal offense to your masculinity if it happens occasionally. Got any other passing tips for long hair? Can you share any experiences supporting or conflicting with this advice? Want to show off pictures of what your long hair looks like?