The Challengers use the standard 2-plug setup so don't get the 5-pin LEMO plug version like the Phenoms and Praetors use. I always use Bose QC35 with the uFlyMike adapter because out of all the headsets I've used in my career, I find them the most comfortable and easy to deal with. Plus, you can disconnect the boom mike and go back to using the headphones as designed while commuting. The rechargable battery in the QC35 and 45s last for days before recharging.
I also carry Bose Proflights (in ear) for spare, but not a big fan of those. I'm constantly fiddling with the earpieces and they suck batteries down after about 20 hours of use. If I could return them, I would. Not worth anywhere near the $1200 Bose charges, but they do sound good and have bluetooth so there's that.
Don't waste time with older Telex 850s either. I have a set of those at home, but they're great dust collectors for now.