From 1997-2007 my hair was never longer than an inch and a half, and for most of that time it never got longer than a 4-guard on the electric clippers. I really loved having it shaved and rough looking.
Since then, I've been on a three-year experiment to see what it's like to have long hair.
I miss the days of 3-minute showers and stepping out the front door five minutes later. I miss the days of 105-degree heat that felt good as long as I was running/biking/walking enough to move the air over the sides of my high-and-tight buzzcut. I miss the days of not having to put a damn thing in my hair, like, ever, except occasionally sunscreen because it was so fuggin' short I'd burn. I miss being able to drive with the windows down without having my hair get in my eyes. I miss being able to lean over and kiss someone without having my hair get in their eyes. Yikes.
The whole point of this kind of thing is to create an external appearance seemingly at odds with my self-concept, and then mine the contrast for personal insight. In that regard, I love the long hair, and I love the constant reminder not to confuse what I look like with who I am. Some days I think it looks good, some days I think it makes me look completely ridiculous, and some days it's just a bunch of stuff growing out of my head. But you know, is that any different than how it is for anyone? Everyone has those days when we think, "Ohhhhh... yeeeah, I am gonna knock em dead today!" and then days when we think "Oh jeez, where did my mojo go?"
I think there's a strong conformity among many homosexual men that tries to approximate an external masculine cosmeticism to compensate for a certain sense of psychosexual lack, whether internal or external in origin. My goal is to throughout my life develop an ever-deeper sense of who I am in essence, regardless of appearances. Then, not only can I make wiser choices about the directions my life should take, I can apply that same facility to attempting to see others for who they really are, instead of just scanning the room for someone who meets a socially-mediated standard of visible "attractiveness" or "masculinity". There are plenty of butch-looking guys who waste money, are manipulative, unfaithful, selfish. Those characteristics are invisible, but I can't think of anything more essentially Manly than being a good steward of your resources, being straightforward and honest in your personal dealings, being loyal to your companions, and seeking the good of others when appropriate, even at inconvenience or pain to yourself.