On ear headphone recommendations

Try Vmoda M80. I got one and really happy with it. Wires got built in mic and volume.

Obviously, you've never learned how to make your in-ears fit right.

It takes some experimentation. Most earphones come with a selection of foam and rubber tips.

The foam tips IME have greater potential for a good fit. I sometimes mix and match tips from different earphones.

You may have sensitive ear canals and never be able to adjust to earphones with a good tight but not too tight fit.

Getting really good bass and comfort out of on-ears isn't any easier to say the least.

Over the ear earphones are more comfortable in the short term, but in the long run it is hard to beat some well-fitted IEMs.

I don't know what price range you are interested in, but if you want some good-sounding over-the-ears for a reasonable price, look at Sennheiser HD 280s.

Depends largely on what you're using it for - primarily walking around, I assume, since you want the inline mic and remote? Also, do you want on-ear or over-ears? Over ears will sound better in general because of the passive noise isolation, but they can be a problem if you're walking around and don't want to get hit by a bus.

The PSB M4U 2 over ears gets universally good reviews, and has an inline remote and mic, and has good passive/active/noise cancelling modes to boot. Only downside is the price ($400), but if I had the money, it's what I would get.

I've heard good things about the new Yamaha Pro line - good sound, good looking and all have the inline remote. The Pro 300 ($200) are on-ear. The 400 and 500 ($300 and $400) are over ear, but if you're spending that much, go for the M4Us.

The Sennheiser HD 280 ($100) and HD 380 Pro ($200) are both really good (both are over ear). The 380s especially are very comfortable for long sessions, and if you can get the it on sale (I got mine for $160) its well worth the upgrade. Big downside for you is that there's no inline mic and remote. I use a Fiio E02i Rocky headphone amp ($30) for those functions when I'm out and about, but it's a bulky solution. Not a huge deal for me, since I use them at my desk 90% of the time, but if you're primarily using these on the go, there are enough cans out there with the inline mic/remote built in that you should go with those.

fwiw, take a look at the audio technica ath m50's. imo best closed back sounding headphones for the dollar priced$120-$150 on amazon and add a fiio eo2i amp with remote and mic. for $28

Good phones that I also have. If HD280s are too closed in for you, then one might think of ATH M50s as being a more open-ear version of a similar thing. The natural trade offs are low bass, isolation and comfort. Can't have all 3 in the same 'phones.

How much you spending? Klipsch Image ONE's are ok, B&W P5's and P3's, V-moda M80's or M100's, and the Logitech UE6000's are better and all have iPod control.

But again I would give IEM's another try, something like the Shure SE215's are nice or the Klipsch Image S4's if you want bass, theres tons of IEM's I would need to know more to suggest one.