I second this. After trying with many different kinds, it's just too big a hassle. Clips at strategic places can help, yet only work so long. Eventually something will snag and the headphones will break. Separate, wireless buds are significantly more comfortable.

I use Airpods most of the time but wired headphones on my desktop because bluetooth is so broken on desktops. Going back to the wired headphones feels like wearing a leash tied to my desk. Want to just go grab a drink from the fridge but I have to mute myself, take them off, then undo it all when I come back.

I'm not sure TWS buds with the shape of an AirTag would work, but I do think they could make them with something like an easily removable cap on the stem that holds the cell in place.

Microsoft was planning earbuds with a big round shape. I don't think they actually ever materialized though.