[PFULMTL]

I use my PRO700MK2's because they are slim and really durable, so my head on it's side is not uncomfortable, but I take them off I fall asleep.

 

[wavoman]

OK this is for side sleepers only: I am one, and I must be sure my ears (actually the one ear that is "down", facing the floor, which of course changes multiple times per night) are not blocked by the pillow for one of two reasons:
 
(1) I am wearing full sized headphones, usually Grado HF-2's, or
 
(2) I am not, but then unfortunately I suffer from night-time tinnitus, so if the ear is blocked my brain manufactures sounds that make it seem like the hulk is walking back and forth in my attic, which makes it hard to sleep to say the least.  When this first hit me several years ago I actually went up to the attic in the middle of the night a few times to see what the heck was up there, until I figured it all out with the help of some medical web sites.
 
Cutting a hole in the pillow might work, but a doctor gave me the following trick which works perfectly for me: roll a soft bath towel in to a cylinder-shapped pillow.  Use that to support your neck and lower part of the side of your jaw.  Then leave a gap, and use your pillow (up against the headboard) to support your head from the top of the ear up.
 
It works, and is easy to reset when you turn from one side to the other.  They sell cylinder-shaped pillows, but they don't work as well for me as the rolled-up towel (which is of course as trivial to wash as a pillow cover).   I swear by this, the hulk in the attic is gone, and I can sleep with the Grados or not, as I prefer.

 

[Lazarus Short]

Have you considered small speakers on either side of the bed?  I used to do that, and good near-field speakers really do give you the best of both worlds.  You have the speakers on stands, and they don't have to play loud because they are only a foot or so from each ear. 
 

 

[JustRick]

I've been thinking about this for quite awhile as I too love to listen to music when I go to bed.  I prefer over the ears headphones and like to lie on my side. I've come up with a good design pillow that could convert to both a normal pillow and one suitable for wearing over the ear headphones, but don't know who to contact about possibly having it designed for sale.  However, I've thinking of trying a massage pillow out such as one that I found on Amazon. My account, for some strange reason, does not allow me to attach an image or I would have, but I think you get the picture. lol  Hope this helps.  

 

[MiLeX]

At the moment I am using Apple EarPods when I am in bed and want to sleep on the side. 
All my other headphones stick way to far out of my ear or are over-ear headphones (I hate on-ear) and I cannot get to sleep when laying on my back. 
 
However, I ordered custom fit in-ears for use in my Motorcycle helmet, I'll try those when I get them later in December and report back how that goes. Only concern I have with them, that I might miss my alarm next morning as they block noise really good.

 

[Peddler]

Apple's Earpods work pretty well in bed but do tend to leak a lot of sound - unless you're listening to music at very low volume levels there's always a risk of disturbing your partner. I have found the 1More Capsule's an excellent choice for listening to music in bed. The fit is really nice and you can comfortably lay on your side with them on.  Hope this helps.

 

[Happy Camper]

http://www.hammacher.com/Product/88520?cm_cat=ProductSEM&cm_pla=AdWordsPLA&source=PRODSEM&gclid=Cj0KEQiA7qLDBRD9xJ7PscDCu5IBEiQAqo3BxLy-cE42XqSXR8_BmwGs_GOaBY7FOFYHlQNCurapL4YaAtNO8P8HAQ

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[jagu]

I have CIEMs (JH13s) and the super small Jays q-jays. I prefer the q-jays when listening in bed. And it's a good sounding IEM too! Check these out.

 

[stephengee77]

With their small size, I like using carbo tenores when listening in bed. They don't feel like much at all, even when lying on my side.

 

[Rearwing]

HiFiMan He-400's are really small and comfortable, and with the correct tips sound fantastic.

 

[H20Fidelity]

I listen in/on my bed basically 99% of my listening time, not necessarily before sleeping, I find I can concentrate on the music more, and my latest edition for sometime is browsing instagram/headfi on my Note 4 at the same time. I've done this so much with instagram surfing it without music is almost foreign to me, and music without instagram, makes me think of instagram!

I use IEM's exclusively but have had some great experiences with Grado headphones due their small cups, Sennheiser HD25 and Amperior as well. The problem I find listening laying down is neck aches and comfort.

 

[Kmackithich]

What about the bedphones ? Looks quite confortable but not in a purpose of an audiophile listening session.
As part of the one-side sleepers, I use earbuds when it comes to bedtime. Unfortunately I find the cable quite stressed in the morning. So I stucked the earbuds between two pillows and push the volume knob louder. I got a good stereo when lied on back, and have still have music when on the side. Main advantage is that sound doesn't leak much and you hear almost nothing when you leave the pillow.

 

[Podster]

Hyperion's

 

 

[Rearwing]

Nice!

 

[flamedrace]

Some nights, I listen to my HE-560s lying down on my back and fall asleep