Koss Porta Pro! It’s no performance monster, but is easily one of the most engaging and agreeable headphones I’ve heard. That and a Dragonfly are a killer combo.
Well you did mention Grados. All Grado pads are interchangeable, and YAXI makes a nice flat purple pad fro Grado. If you can go with the Grado RS1E, you won’t get the signature high end on the Grado, and it has great sound stage. Good bass with the L pads - I have not tried flat pads on mine. You might look for a used pair.
HD-25 is interesting. I don’t know anything about them so I’ll look into it.
One of the reasons I’m looking this direction is the old PX-100 portables that I used for a long time. I became accustomed to the driver being in the open air without a cup. Too bad those are not made anymore.
I didn’t know all Grado’s could use the various pads. Of course it probably changes the sound a bit but I could poke around and see which models are closer to Harmon.