I'm starting to lean towards just grabbing a HD600/HD650 and a portable amp (probably second hand HD600s if I can as they're apparently easier to drive). Looking at a few pics of them, they look passably nerdy to walk around in ... plus they're Senns so they're instantly more acceptable
I mean, HD-25s sound great but they're maybe $50 cheaper than the aforementioned. Besides, even if I can't get them to sound the best with a portable amp that gives me upgrade potential for a home rig later on. Sure, they're not closed like the HD25 but I'll live with that I guess.
ES7 sound interesting too but a bit on the cheap side, think I have enough $50-100 phones already thanks for the suggestions though