Comments for the OP:
1. Agree Senn PX-100 are excellent, they got my into this game in the first place. But they are open, which can be a no-no in certain places. Their closed sibling, the PX-200, does not sound as good. Best folding closed can I have found so far is the AT ATH-ES5.
2. With these, or good IEMs (I have Shure 500), portable is worth it, and an amp makes a big difference even to these old ears (and everyone else at the gym or the office).
3. A Predator (or Pico) and an i7 (or similar), cabled with an IC and lashed with velcro, fit in the tiny soft camera cases sold everywhere and easily fit in a pocket, ready to play. I leave them both on, set to shuffle, and simply hit play, re-zip the case with the HP cable just sticking out where the zipper closes. No sharp corners, and I can do this while the treadmill is moving. No exposed metal, no problem not being seated. You're not trying hard enough.
4. If you think an iQube is "poop", you are reacting to something other than its SQ. For "serious" portable listening, like on a friend's deck with two phones and a Y connector, the iQube and my RWA 5.5 Gen (Wolfson DAC) iMod with uncompressed files is damn impressive and has power to spare, driving both. This rig goes with me on long vacations too. Wife brings portable Panasonic cans that are junk, but have an attenuator in the cord, so we both can listen at our chosen volumes. Looking out the big Ahwahnee Lodge window at the Yosemite mountains by moonlight at midnight, you and your girl (wife) both listening to the same "right" music is magic man, I guarantee it works.
Oh but you're giving up on this stuff, sorry. You'll have to use your good looks and charm, neither of which I have.