I own at least ten pairs of headphones, as well as some small amps and a DAC, but I end up going back to the $19 Aukey Bluetooth earbuds from Amazon. They sound good enough, battery still lasts 5 hours and they must be six years old, and they're cheap enough where I don't care if they are damaged or lost, but I haven't managed to lose them.

Sure, on an airplane I'll drag along some noise cancelling ones, and I keep a wired set of Sennheisers in my bag for a backup, but I never use them otherwise.