I use these. Super small, they never bother my ears, unless I've been in bed for 14+ hours.
I've heard the headband ones are not good; I forget why but the Amazon reviews motivated me to buy this one instead. I found it to be extremely comfortable to wear even while lying on my side because the bud part is almost completely soft, no hard part. The sound quality was good enough for asmr. The downside is that mine stopped working for no reason after a year or so, so it was not that long lasting. I'm okay with that since it's relatively inexpensive and easy to replace.
I have Maxrock ear buds. I fall asleep on my side they are super comfy. The only problem is waking up in the middle of the night tangled up in the cords.