I'm using the Playstation Gold Wireless Headset for pretty much anything ever since I got it. I like how comfortable the thing is while wearing it. Even though I wear glasses I can wear it for a long time without feeling discomfort. I also like how it has a 3.5mm jack that pretty much fits into anything. Not to mention the bass is just right for me.
I know this is a Cliche brand, but Bose AE2w Bluetooth headphones I think are the best kind of headphones. I love using them for running since it drains out pretty much all the sounds you want it to drain out when running.
I don't really have a brand preference just yet but I've always preferred in-ear...I'm okay with hearing either way but that way helps me to tune out outside noises more and completely focus on whatever it is I'm listening to. There has gotten to be a pretty massive variety to choose from though- I'll have to check out some of the brands you guys suggested .
If I had the money, I would automatically go for Bose earphones: their products are simple, yet produce such clarity in audio, it makes crappy mp3 files sound almost live. But until I can afford such a high-end product, I'll stick to the layman products at local yokel electronics carrying stores.
Just as an update to what I said before, I recently got some Beats earphones. I'm pretty sure they're knockoffs, I don't think $40 is anywhere close to being legitimate for Beats that would normally cost $100 but whatever, they work better than my $15 Sony earphones so what do I care. If you're going for earphones, Beats are the best though. They catch all the different parts of the song very well, and it's worth the money in my opinion.
If your head is on the larger end of the spectrum (mine is) I would recommend getting a recommendation from an audio store. In my area they can even swap out the headband on some of the models. It really makes a difference especially if you get a fixed headband, because it feels much more solid than an adjustable headband. Plus, it doesn't fall off as easily.