Good morning! I was in the process of researching health information when I came upon this forum. As I read through posts, yours caught my attention and I thought I'd add my two cents! :)
It sounds like you already a few ideas of possible causes of what may be causing your headaches. Before going through a lot of medical testing, appointments and probably money, I'd try eliminating those possibilities first. Stop wearing anything on your head, give it a week or so, and see if the headaches are still there. If they aren't, add in one thing at a time for a few days, until you come across what triggers your headaches. However, if after that week, you are still having headaches, you'll need to weigh your options about whether or not they're bad enough to warrant medical attention.
Also, with the fact that you mention you get them especially at night, in reference to moving your head/eyes things like that, I would also wonder if you need glasses (or if you already wear glasses, needing a new prescription).
More than anything else, go with your 'gut instinct' in regards to seeking medical treatment. I've watched two family members and my childhood best friend deal with these situations. My best friend had horrible migraines (or what they thought) for as long as she could remember. They'd get so bad, she'd have to be in complete darkness, no noise, a cold washcloth on the back of her neck and then (not sure how this helped) but a clothes pin clamped at the bridge of her nose. She stayed like that until she'd start vomiting, and then it would go away within an hour or so. I watched as her parents would blow it off, tell her to suck it up.. all kinds of BS believing she was simply being a drama queen. It wasn't until she was an adult with her own medical insurance that she finally was diagnosed with a small tumor at the base of her skull. It ended up being benign, thank goodness, and a quick surgery fixed the problem.
My uncle experienced similar symptoms, however he ignored them. Finally, one night on his way home from visiting my grandmother, he had a seizure, rolled his truck and damn near died. Once taken to the hospital, they found he had a fractured skull from the accident. Strangely enough, if he hadn't fractured his skull, the doctors would have never found the tumors in his brain. And then the worst of all was with my mom. On Dec. 30th 2011 she'd experienced the 3rd headache in a week that just seemed strange. They only lasted about a minute, but they just seemed strange to her. Once admitted, they performed test after test after test which all kept coming back normal until they performed an MRI with contrast. That's when they finally found five lesions on my mother's brain. She was actually diagnosed with two forms of brain cancer... Oligodendroglioma and Glioblastoma Multiforme. Even with surgery, radiation, chemotherapy and a few other forms of treatment, she lost her battle 7 months and 3 days from the day she was diagnosed on Aug. 1, 2012.
Please understand I am NOT trying to scare the hell out of anyone... but if you feel something is wrong, address it with a physician! The worst that could happen is that you have to pay a bill for a visit that tells you there are no issues to worry about!
Always be your own best advocate!
Good luck to you!