Just participated in the recent drop for the Magaosi X3 (I'd pass), but they have a shell that fits and isolates like it was measured just for my ear. I can't sleep with anything on my head or ears but I've been able to doze off with these in my ears because they're that comfortable. They also isolate so well that I'm on the bus with the Bluetooth volume up 3 steps and I can barely hear anything outside of my music.
Are there any other IEMs like that out there? I see that the MD x Noble Plus has something like that but I'd probably like to keep it below $250 if I can manage it.