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over-ear headphones vs IEMs

Yes, I'm using the Audio Technica ATH M-50. I had a producer recommend these because he used them for tracking. Ive had them almost 2 1/2 years now. I stopped using IE's cause they hurt my ears, not from volume but just the pressure of something being in my ear for so long. They weren't molds just buds. Most of the time we play 2 1/2 to 4 hours and they never bother my ears, I usually forget I even have them on my head. I'm pretty happy with these considering how much they have been used and not failed me yet.
 
When I'm mixing, I have a set of Senn HD280Pros sitting by my console at all times. For the price, they're the best sounding, most comfortable Supra-aural phones I've been able to find. That said, on stage I'm IEM all the way. Partially it's from an aesthetic perspective... wearing cans on stage would look a little weird to me. Also, I tend to move a decent amount and cans would likely fall off. I've been using UE Triple.Fi 10s for about a year and while they sound awesome, they're about the worst fitting universal IEMs that I've encountered. Just sent them in for a custom reshell, and I think that might set me for life. I plan to use them for everything except mixing (on stage, casual listening, biking, ignoring co-workers, etc.).
 
I've tried various open-back and sealed cans. None of them really worked for me, not enough isolation or clarity. I was trying good stuff, too - AKG, Beyer, Sennheiser.

I would suggest getting custom molds, or trying either the Shure black olive or Comply foam tips to improve your comfort with your existing in-ear buds.

I use the black olives with my Shure 425SE's, and it gives me a comfortable fit, plus a very clear representation of the monitor mix.