[DrunkenTiger]

Earbuds feeling uncomfortable more and more, maybe just need better ear tips though... (JVC FXD80, Zero Audio Tenore)
I run a clip+ rockboxed or listen from my surface pro 3 when I'm not at my desktop.
Might get a Fiio X1, not sure though.
 
I listen to a mix of music and I'm not a basshead so it doesn't have to be boomy necessarily.

 

[KG Jag]

If in (or buying from) the USA, the NAD VISO HP50 is within your budget.  See:
 
http://www.innerfidelity.com/content/i-love-these-headphonesthe-nad-viso-hp50

 

[billybob_jcv]

How portable is "portable"? Do you just mean able to be driven directly from a smartphone, or do you also mean very lightweight & foldable?

 

[squee116]

How portable is "portable"? Do you just mean able to be driven directly from a smartphone, or do you also mean very lightweight & foldable?

A very solid question.  I have the PSB M4U1, the precursor to the NADs mentioned above, and find that they work GREAT without an amp, but are a bit heavy and bulky for "on-the-go" use, at least for extended use in that category.

 

[DrunkenTiger]

How portable is "portable"? Do you just mean able to be driven directly from a smartphone, or do you also mean very lightweight & foldable?

Definitely the first part (I did mention my playback sources after all), and yeah reasonably portable would be nice. Which is why I'm considering on ears as well as over ears.