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I get a little (maybe a lot) OCD when it comes to keeping my headgear clean. IEM cables will get wiped down with a scrap of paper towel and alcohol, especially if it's a hot day out. The tips I figure actually don't get as oily/sweaty as cables, but I will wipe them down on a cloth (or my shirt) after every use. I'm usually pretty good at swabbing out my ears regularly, so never have issues with wax on the tips.
With headphones, I'm even worse. I *hate* the feeling of grime, and I already have oily skin to begin with, so velour pads are straight out. Leather or pleather for me all the way, and even then I take them off a couple times an hour to do a quick wipe on whatever cloth I have handy (usually a small terry cloth I use as a wrist wrest with my mouse pad, or my shirt). If I'm at home and have the luxury of time, I'll actually give my face a quick wash. If I've been doing yardwork or something and am sweaty, I won't put on my good headphones at all. My best time for listening is in the evening after I've showered and feel "clean". This is pretty much the only time I'll wear velour earpads if leather isn't an option (such as with the Sennheiser HD650).
When I sell used gear and say they are in good condition, I mean it!