[yello131]

Radius DDM is great for Jazz

 

[BRCMRGN]

Meelec M6, Sennheiser IE7, UE 700, UE SF5, CK10. I can sleep with any of these.

 

[JeFFz]

the sennheiser ie8 are flat enough for you to sleep on the side, but you will still feel some intrusion.

 

[MrBassmicks]

I was just about to make a thread like this. Its nice to find one with replies already in it.
I love falling asleep with headphones in. But the tip on my JVCs keeps falling off and getting stuck way down in my ear. And that's not fun to deal with when your half asleep at 3 AM. So in addition to OPs criteria as far as comfort, are there any headphones that hold on to their tip very well. 
 
Not trying to thread-jack, I just don't want to make a whole new thread for a slightly different question.

 

[TopspinTEC]

+1 for PL50s.  They are very low profile.

 

[nyjets28]

+1 for westones

 

[theleonlion]

I would recommend purchasing a pair of earbuds. Honestly, the pressure buildup with an IEM may cause damage or infection (if your tips are dirty) to your ear if used nonstop for hours.

 

[T78Power]

I sleep on my side with the UM3X and with the W1 and UM1 being smaller I think that would work for you.
 
Also I've been thinking about getting some CHEAP phones for sleeping though. No use risking damage to a high end set.
Something like the JVC Marshmallows they sell at walmart etc?

 

[qawsedrf]

I echo theleonlion's suggestion, you oughta consider earbuds.

 

[h8uthemost]

Thanks a lot for all your help, guys. This is more than what I was hoping for.
 
And yeah, since I already sleep with my stock earbuds, and I know those are pretty comfortable to be used on your side then I might just go with another pair of these. Although, I really would like to have something with a little better sound quality. Is there anything in earbud route that sound really good? I don't want to go too high end, because like T78Power said, no use in damaging an expensive pair just to sleep with.
 
Think I might get a pair of Westone's just for all around use(maybe, I prefer cans for this type of listening), and then a pair of earbuds to sleep with.
 
Thanks again.

 

[T78Power]

Well, these aren't earbuds but some cheap in ears I'm considering for use when sleeping.
 
http://www.amazon.com/JVC-HAFX35AN-Marshmallow-Ear-Headphones/dp/B004I44CU8
 
http://www.amazon.com/MEElectronics-M6-CL-Sound-Isolating-Headphones-Players/dp/B0038W0K2U

 

[Sayajin]

One more vote for PL50. Great ear-gasm in the night.

 

[theleonlion]

I use either my Sennheiser MX580 or my Apple iBuds to sleep.
 
You could invest in a pair of 9Wave earbuds.

 

[DaBomb77766]

I think the soundmagic PL50s are perfect.  They fit really flat in your ear, and have a flat outer casing.  You can sleep on your side no problem.  As an added bonus, they're relatively cheap so you wouldn't have to worry too much about breaking them by sleeping on them.  I personally wouldn't wear really expensive headphones to sleep, but I guess that'd be up to you.

 

[h8uthemost]

Nice recommendation, theleonlion! I forgot that Sennheiser makes a small line of ear buds. And on Amazon the MX580's aren't expensive at all(about $30). 
 
As for the PL50's, those look like they might not be all that comfortable to sleep in. And where in the US are the 9Wave's sold? I can't find them or a price.
 
By the way, how is the sound quality of the MX580's? They gotta be a step up from stock ear buds, right(eventhough I think my stock Cowon buds sound way better than stock iPod buds)?
 
EDIT: Oh wait, what am I thinking? I have a pair of Sennheiser CX 300-II's that I thought sounded absolutely fantastic for the price. But I accidentally through them in a candle, and one side got doused with wax and no longer work. And since I don't have the receipt anymore(bought them in a store a couple years ago) I can't get them replaced. I'll pop those in and lay down and see how they fell. They don't portrude out of the ear really none at all. So as long as those feel ok then maybe I'll get another pair off of Amazon.
 
Anyone have any experience with the CX300-B's? They're only $30.