[JT1320]

I want an upgrade from my old PX100; comfortable on ear portables that I can run off my Cowon J3 without an amp. The genres I listen to are progressive and alternative rock.

I don't like the feel and complete isolation of canal phones. They hurt for me since I have really small ear canals. The only thing I can handle in this category are the oval tips of the Klipsch's and I already own a pair. I also want to be able to have a conversation with someone without taking them off - something I can't do with IEMs.
 
Some other aspects I'm really looking for are:

1. The size of the headband - I apparently have a really tall head. My PX100 and portapros, with the headband fully extended on both sides, are just long enough to fit me perfectly. In the past, there have been many times that I had to return my cans to the store just because the headband wasn't long enough for me. A few examples of this are the Shure SRH750, Sennheiser HD228, AKG K450 (K420 fit me though), and the Audio-Technica ATH-NC7b.
2. The comfort - I have to be able to wear these for hours on end. I also have a pair of portapros which I don't use that often because it lacks the padding on the headband the PX100 has. Clamping force is also an issue since I wear glasses.
3. The sound - I have a pair of Image S4s I can use if I want excessive bass. With this pair I'm looking for something more natural, but not completely dead flat; I want a pair of cans with a warm and rounded bass/mid with detailed the highs my S4s can't provide.

 
I'm thinking of spending $200-$300. It would also be nice if I don't have to find extra pockets to stuff a couple feet of cable while I'm on the go. Looks are also a bonus. If it attracts the ladies, then why not?

The cans I've been looking at so far are the HD25, ESW9A, and the T50p. Any suggestions?

 

[swbf2cheater]

Well, you definitely picked the best out of the crop to look at.  This is an on going debate with no clear answer right now, but I am going to lean towards the t50p being the best in every way
 

 

[JT1320]

So any of those 3 would be good?

How about the size of the headbands?

If anybody reading this owns a pair of PX100 or portapros and one of the 3 the headphones I mentioned, could you see if the headband is long enough for me? Both the PX100 and portapros headbands fit me perfect when fully extended.

 

[JT1320]

Nobody has a PX100/portapro and one of these headphones on hand?