How to find comfortable headphones is to focus on the fit. The one thing that we may not associate with headphones is the comfort factor. There is a lot of information out there about headphones but no one every says that you should actually “try it first before you buy it”. The key is to be comfortable and still be able to do what you want while taking in the sounds of your favorite tunes.
What are you looking for as far as comfort goes? If you think that the sound has to be right inside your ears then this is a good place to start. You should make sure that your headphones sit perfectly on your ear for the maximum comfort.
It is going to be up to you to decide what is going to work for you and your music needs.
The circum style will lay around the ear and give you a muffled sound like if you were sitting in an auditorium and the supra style will seem like the instruments are next to your ear for sure.
You should always make sure that they are comfortable before you purchase them. Many of the headphones will have leatherette type material on them to cover the plastic for the hotter weather. Some have velvet pads to take care of this problem as well.
Some of the portable headphone sets will have the ear bud type of headphones. These are not very comfortable and like to fall out sometimes. You may want to think about trying something else instead of this route before you make your final decision.