Beyerdynamic DT 880's, or more comfy Grados?

[blackinches]

I'm ready to move to some finer headphones--my current budget headsets are no longer cutting it. I prefer the sound of my Grado SR-60's with bowls to my Sennheiser HD-280 Pros. However, I can't stand to listen to the SR-60's for longer than a couple hours due to discomfort.

I'm looking at Beyerdynamic's DT 880's, AKG K 701's, and Sennheiser's HD-595/600/650's to be paired with a β22. Eventually, I bet I'll purchase them all. However, I can't decide which to try first...

Should I consider some of the high end Grado models (SR-225 or RS 1)? They look just as uncomfortable as my current Grados

[Tomikans]

have you soaked your bowls in hot soap water? It really softens the pads. They made my pads much more bearable.

[blackinches]

It's not so much the pads that bother me. Maybe it's the shape of my ears. The pads and drivers feel like they're cutting off circulation in my ears. The original pads weren't comfortable either, but I'll give that a shot.

I can listen to my Sennheisers endlessly, and I've heard Beyers are comparably comfortable.

[Aura]

Maybe consider some Grado C-Pads from headphile.com (or make them yourself).

They are essentially wood adapters that allow Beyer pads to be used with Grado's. I'd like to try them myself somewhere down the road.