A couple of weeks ago I had to endure a night with bog-standard ipod phones. For a side sleeper, that was torture.

I have looked into the higher end shures, by they all seem to protrude to long to offer comfort when sleeping on the side. But for you are awake, I am sure they offer better isolation and sound. I would like to have a tiny speaker element that you could fit in an for ear plug and add a silicone mouldable (I use the US brand Mack's) earplug as a cover.