best over ear headphones-stuck at a cross roads!

I cannot STAND over ear headphones!! Vvvvv antithetical to this sub and what I’m asking for. BUT. I hate earbuds even more, completely non functional for me, they keep falling out, doesn’t matter what size rubber tips I get.

So I switched to over ear ones, but new issues. HEADACHES. I have a pair of Oraimos currently (boom pop lite) and I’d heard their band was extendable and cups were less vacuum sealy. BUT NOPE. still struggling with the pressure on my head and it gives me headaches. It’s not even that I have an abnormally large head, it’s about average for a 5’5 woman. But I can’t live without something playing, my ADHD just goes out of control during work, it’s so fkn mindless.

So I’m here to look for solutions, and maybe new headphones? I did some preliminary research myself, I’m not completely useless and I’ve made a shortlist based on band size.

And other than that I’ve been looking at ratings online a lot, like comparison websites. Narrowed it down to Bose and Sony (wanna spend some good money, the oraimo ones were my boyfriend’s) and i’ll include a screen shot, the ratings are good. But not great for the Sony ones, WHY. and the website won’t let me click on the listing itself so i can’t figure it out.

Please can someone help me????

Should I be looking at gaming headsets? I’m assuming those are more comfy cos you do have to wear the for longer stretches at a time.

I also tried looking up ways to make my current ones hurt less, but it was just things like give your ears a break or I might have pressure based headache patterns. Any advice here is welcome too.

Oh and for the rules, my budget is around 250+ dollars and I can order online on amazon, in person is tough.