First post! Sorry it had to be a negative one ...
For basic comfort, the silicone comfort ear tips on conventional (no ear clip) canal phones can be very straightforward and comfortable. For noise-cancelling in-ear monitors, foam ear tips can be very comfortable and more noise isolating than the silicones.
One suggestion: look into the Etymotics ER6i's for about $80 - $89 online. When used with foamies (extra expense, but worth it for many on Head-Fi ... the black Shure foamies last much longer than the other brands out there currently), they are very light, small and comfortable. No clip and not even a wire worn over the ear (unless you want to). There are others to choose from, of course. I hope you get some good suggestions.