My Bf and I haven't tried many different kinds of condoms so I do not have a broad view.
Ribbed I found harder to get in on original penetration, but afterwards there wasn't much difference.
Normal with lubrication are the ones we normally use and I have no problems whatsoever with them.
Normal without lube are the worst I'd say. They are TERRIBLE for initial penetration, and if you start to dry up, or if you go to change position and it drys as you move, it hurts again.
My ultimate favourite would have to be the smelly kinds. We have tried banana, and strawberry. After sex the whole room smells so yummy. The banana ones made it smell like we were baking banana bread, and the strawberry ones smelt like candy.
If you really want to find out, why don't you try some out. You can get multi-packs, or you can get strips of three of a certain kind.
Hey I think that would be a fun experiment