Getting a proper fit for in ear 'buds can be a real challenge. Like more than a few people, my ears require different sized tips for proper fit. One ear uses medium tips and can use either the conical or spherical shaped tips, but only if they're foam, memory foam preferably. The other ear uses a large tip, and it has to be conical, not spherical.
The triple flange type (usually silicone) hurt my ears after an hour or so.
I will try the AirPods. I don't run, so no fear of losing them. Not having wires means less weight and no pull on the 'buds, and they should be more comfortable over time if the initial fit is compatible. However, sound isolation will not be great. That could be a good thing for street use, but I like to filter out the noise for at home/work listening, and especially on public transportation.