Plenty of guys have long hair. Most of them keep their hair long because they're too lazy to get it cut. Guess how much time they put into styling it? Forget everything you know about hair.
If your hair is straight, ponytail. If your hair is curly, braid. That's it for 99.9% of men's (very) long hair styles. The ponytail should be sloppy, and the hair tie should be as low on the head as possible, right where your head turns into your neck. Same goes for the braid, except you don't need a hair tie up top. Since an additional hair tie requires more effort, you definitely don't want that.
Okay, now your hair is done. Go to bed and don't mess with it in the morning.

(this may be sarcasm, or it might work for you)
If you're a gross boy like I was, don't bother taking the braid down for the next month. Then, the split ends will just break and break and break, and your braid will be a thin whippy rat tail at the end in no time at all.
All that said... my wife has done drag a couple of times, and tried to style her hair as above. The result wasn't great.
If you want an intermediate-length hair cut, cut it straight at the shoulders; no layering, no funny stuff.
One thing to know about being a teenage boy with long hair: people are going to misgender you. Maybe a lot. It happens to cisgender male teenagers, as well. A lot.