it depends on what you want to listen to.
with ear buds.
open backed headphones will loose sound, meaning that you have to turn the volume up.
open backs increases clarity at some frequency ranges, this means that those ranges appear louder.
open back also tend to have less isolation, which means that they are better for cyclists as they can stay aware of their environment.
silicone tips do provide some security (as in they help them stay in your ears more than isolation on open backs.
sealed units tend to lack clarity in bass notes, and often rely on the silicone tip producing a tighter seal in your ear so that they can transmit bass to your head rather than playing it in the air.
the three cup tips, personally I find uncomfortable, if you've got a pair of headphones like this that you find uncomfortable. try cutting off the cups until they are comfortable, but be aware, the reason that they are uncomfortable is likely that they are made to be forced into your head, to transmit bass, the more cups you cut off, the looser (and more comfortable) the fit, but the less bass you'll hear too.
it was the mid 90's when we first saw ear buds with bits that extend into the ear canal, basically anything making contact with your ear canal is going to improve bass response when compared to the same driver just resting on your outer ear.
personally, I find anyone claiming to be an audiophile and showing ear buds in the same sentence to be a massive nonsense.
if you're a real audiophile then go for proper over the ear cans, they have a decent sized driver that's capable of producing all the frequencies that you're interested in. they tend to have foam surrounds and so isolate noise well, (not as well as closed backed ear buds that also seal your ear canal with silicone tips though).
even cheaper over the ear cans have as good audio performance as a lot of people claim to be getting from mid priced ear buds.