Sam naturally holds his head high - he's got a bit of an upside-down neck, with all the muscle on the bottom, and if he's exited, it's in my lap!! Sometimes, though, if he's worried about something on the ground in front of him, he arches his neck an his ears are two inches apart!!
I ride him English, with a martingale, and he's getting better - today we worked on giving to the bit, which he did very well with. I'm just working on Sam's headset so I can have a horse worthy of a home video taping: he's just a pleasure horse, so it's no biggie.
If you want his head up, I'm not sure quite how you do that - I'm better at going the opposite direction!