[SilverBlade]

So...I tried the Koss Portapro. 
 
Immediately...didn't like them.  I have a large head and they were tight on me, even when the headband was extended to it's maximum.  (I even tried the Sennheiser PX 100 - it clamped on me so tight that my ears felt like they were going to bleed)
 
Plus the sound on this wasn't nearly as good (to me) as the headphones I'm trying to replace (Sennheiser pmx 60 - which I loved)
 
Would the HD229's be a suitable replacement?  

 

[jekostas]

Have you considered clip ons? I'm in much the same boat as you with a large head and they worked for me.

 

[SilverBlade]

I've never tried clip-ons, mostly because when I look at them, they look like they would be a pain to use.  They look like (to me) that they would always get tangled up in itself.  That's why I've always liked the 'behind the neck' style.
 
Plus, I when I had the PMX 60's, I loved them.  I would either want equal sound, or better sound.  The Koss clip-ons...don't look like they could be as good as the Sennheisers I had.