I don’t think bone conduction would work well for music and work headset. I need to get away from the overhead band as my scalp is reacting badly to them as the temperatures rise.
IEM’s are uncomfortable…earbuds may work, but I’d prefer something that allows for a sturdier placement like a wrap around neck band. a microphone would be nice, but isn’t a game breaker if it doesn’t have one. of course, that’s assuming there is anything worthwhile out there.
If iems, earbuds, headphones and bone conduction stuff are not viable for you. You pretty much only have those neckband speakers (not viable if you cant have sound leaking to your environment) and stuff like the Sony Linkbuds and Huawei FreeClip.
I know the style you’re talking about, and I don’t think anyone makes them anymore (used to be pack-in headphones with Discmen and the like); I know that you said headbands were an issue, but what about lil’ tiny ones like on the Koss Porta-pro or KPH-40? They’re very slight but secure, and with the KPH-40 you may even be able to just let the headband rest on the back of your neck instead.
I forgot about Koss…they do have several options that I can consider. I’ll just have to remember to keep my head shaved because my biggest complaint for the one’s I’ve had were how they pinched and pulled it when longer, LoL!!!
I too have known that pain, but I keep my hair real short in general (like sub #3 on a clipper); I find that with practice, you just kinda learn how to put them on and take them off while adjusting to prevent ripping out the sod, as it were.