headsets / sunglasses
I had the same problem a while ago. I bought a cheap and nasty headset which in hindsight was a total waste of money. The headband would dig into the top of my head and on any flight over an hour it would start to get painful. Also the legs of the sunglasses would dig into the side of my head. I found that putting on the sunglasses first and then the headset was a big help, instead of the other wat around.
In the end I ditched the headset and got myself a pair of David Clark's, I have never looked back. The sunglasses are still going strong.