[MadJack820]

I'm looking for a pair of over/on ear headphones for running/ working out for ~$50 or less. I'd like them to be relatively comfortable but secure. I can tolerate a pretty strong clamp from over ears so that's no issue for me. Sound source is my phone/ zune so while I don't want stock ipod bud crap, I'm not looking for high quality. I mostly listen to house, rap, trap, and trance during workouts.
 
I can't do IEMs when I run because they never stay in my ears, I've spent too much money on different pairs and tips. I've got these small ears (and I guess awkward canals) and custom tips aren't worth what I need these for, so please don't recommend any IEMs for me. Wrap arounds and ones buds/ headphones with clips usually don't fit me well either because of the small ear thing.
 
I just need a snug and tight fitting full-sized that aren't going to fall off when I run or when I lie down to do bench press. Thank you.

 

[halfinfinity]

How about the Koss Pro DJ100's? For the price the quality is outstanding. They are available on amazon for $45. Real sleek looking too. I can't guarantee that they will stay on your head, but with over ears, and in those conditions, who can? Not sure what else to offer you in that price range. Only thing is they have a coiled cable. But I hope these fulfill your needs. They really do have superb sound quality. You will definitely like them a lot. Give me a bit of time and I'll see what else I can come up with. For now, I hope this helps. 
 
-halfinfinity.