[QUOTE=OpalCat]
The reason I don’t like earbuds is that having something in my ears makes them hurt pretty bad after a relatively short time. I have weirdly sensitive ears (very stiff cartilage that doesn’t like to be bent out of its natural shape even a tiny bit). I have been woken from a sound slumber by the almost intolerable pain in my ear because…gasp…I was laying on my side with my head on a soft comfy pillow, squishing my ear. That given, the in-ear monitors probably aren’t for me.
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Given this, you’re probably going to want the “circumnaural” type, these have pads that sit against your head around the ear, and not on the ear itself. These are the most bulky, but IMHO the most comfortable type for extended wear.
My only direct experience with noise cancellation headphones is with the Bose. They were pretty effective overall, and had pretty good sound, and seemed pretty comfortable to wear (I only wore them for about 10 minutes, so my experience with the comfort factor is limited). But they are pricy, as I recall they were around $300.
The thing about headphones is the comfort factor along with the sound. Comfort is so individual, that a set of phones that I can wear all day might give you a headache in 30 minutes. I listen while sitting quietly almost all the time, so I have no problem with ones that might slide right off your head as you walk. There are reviews of course, but nothing replaces getting out and trying a few on for 20 or 30 minutes.
For sound, low noise, good sensitivity, and overall flat response are important, but that still leaves room for plenty of individual taste. I’m older, so I need extended high frequency response. I listen to mostly R&B, soul, or light rock on the headphones (when I go to the harder rock, I like to feel the bass, so I go to the speakers) so I don’t need super high volume, instead I go for more dynamic range.
I personally have Sennheiser HD600. They are great headphones but are not noise cancelling, and are again kind of pricey. I wish I had more direct experience with the type you’re looking for, but I hope you find some you enjoy.