A man after my own heart
My own headphone behaviour is uncannily similar to that of Mr Dabbs.
I look at headphones in the shop when I don't need any new ones. My preference is for over-ear designs, except they are incompatible with my hat which I wear anytime it is raining or likely to rain... or sunny. I have preemptively reinforced the cable near the plug on various 'phones with Sugru, Sikaflex or heat-shrink tubing. Indeed, this cable issue is why I don't have a problem with a cheap dongle on the end - let an inexpensive doodad take the mechanical strain, be it 3.5mm > 3.5mm or otherwise. If I broke out the soldering iron now, I could repair at least four pairs of 'phones I have kicking around.
I'm mildly upset at leaving my plastic over-ear Sennheisers in a pub the other week - I could fall asleep wearing them, and yet feel no discomfort on my ears when I woke. Still, I'd only taken them out of the house because I had lost or broken all the pairs of earbuds I've had.
I would never buy anything akin to Apple Airpods- far too easy to be loose if you're me. Might be tempted by the 'neck bud' form factor.
Keep hearing of cheap but very cheerful Chinese ear buds... think I'll consider them to be consumable items like drill bits or knives.