When I got my first iPod, the 20gig click wheel - I tried to apply the black earbud covers which came with it. I think it came with two sets of covers even then. I tore the first one fumbling with it but managed to get the other one on. The torn one was uncomfortable and the earbud kept falling out - really, really annoying.
I removed the covers and used the earbuds without the covers since then. The sound was okay, but I simply could not keep the darn things in unless I didn't move at all. Not likely since I am a fidgety. I got the iPod at the Chicago Apple store while attending an Apple administrator course. While walking back to my hotel I saw a Sony retail outlet a few doors away. I paid $150 for the lightweight noise-canceling headphones. They stayed put and work pretty well on an airplane, but they make my ears sweat.
I just got a new Video iPod (watching movies is much easier to manage on the plane than on the Macbook and I can jam it full with 100's of my favorite TV shows!), which also came with the same white earbuds and little black foam covers. I thought I'd look to see if there were any instructions on how to get them on the Apple site. - nada - Went to Google it and found lots of complaints about the covers falling off or replacements, but no instructions on how to use the Apple ones or get them on the earbuds at all.
Here is my solution for applying the covers. I hope it can help someone. With the aid of the "Popsicle Stick" they slide on easily, and you don't over-stretch the foam which makes them loose and fall off rather quickly. The earbuds stay in my ear now and are actually quite comfortable. I thought I had a deformed ear hole or something, they kept falling out before. I don't remember the first ones I had, sounding this good.
I wonder if I can get something from Apple to fix my deviated septum?
(click on the first image then step through the process)