Best on-ear headphones for long listening session?

I'm trying to upgrade my earphone to headphone, just for nice bass and comfort. I had no idea about headphones outside DJ headphones, I am actually considering the Sennheiser on-ear ver.2 headphone. Should it be more than enough regarding the price? Not sure if it's pretty much suitabe for long listening, but I wish to have something that can help me with music observing and studio monitoring. Budget < 300USD.

Thanks

Hi,

I have the boomphones. Over your esr headphones with built in soewkers on the outside, although not amazong quality spewkers, the headphones are i must say are unbelievable! They sound quality and they have a little switch you turn on to activate increased bass and treble/high!

Have a look at them!

Bose QC20 or QC20i. Hands down the best in ear headphones at that price range I have ever tried.