My personal favorite of all the ones I've had is the Google Pixel Bud Pros. Comfortable enough I can sleep in them, even though they do tend to fall out. Next fav was the Sony LinkBuds, stay in well when running and didn't hurt too much, but batteries died way too early.
A friend talked me into buying the latest Samsung Galaxy Pro 3 buds, which a lot of people rave about the fit on, but for me they are VERY uncomfortable, even with some premium small memory foam tips. But I keep them because the sound quality and features are still better than anything else I have.