[posnera]

I've got a pair of TF10 from the Amazon sale. They just aren't comfortable enough, especially if I lean on them. I will be using these for travel, so sleeping with them in is a real possibility.

I was planning on sending them for custom shells to Fisher, but if there were a stock universal with similar quality but better fit/comfort, I would rather not bother with the customization process.

I'd like this thread to focus on comfort (I know that it is very subjective, but there are plenty of reviews here which discuss sound quality).

So - are the W2 comfortable to lay on? Any other options?

 

[Dekimasu]

Audio-Technica CK10 are small, as are the Grado GR-8. And both are light and comfortable, and in your price range.
 
To a large extent, what you can sleep on comfortably depends on how big your ears are...

 

[yliu]

Klipsch image X10 or X10i, maybe a little over your budget but they are super comfortable!
All the Etymotics are comfortable too if you can get used to it, but many people can't get used to the deep fit.