With headphones/headsets I think it's a good idea to go to a store and try out different types so you know what suits you best. There are pretty big variations in what people find comfortable to wear.
There are also preferences with respect to the amount of bass, some headphones are more bassy than others.
A good starting point:
Steelseries 5H v2 $100
- large circumaural design, should be easy to wear for almost anyone
- can use either the standard 3.5mm connector, or inbuilt 7.1 virtual surround via USB
- sound quality is OK, nothing spectacular but decent enough for gaming; if using 3.5mm you can tweak around with the sound driver's equalizer to find a sweet spot
- has microphone
If you can pay more:
Sennheiser PC360 $180
- well rounded sound quality, but not too bassy; can be corrected with equalizer if needed
- excellent noise-cancelling microphone
- works wonderfully with Asus Xonar & Dolby Headphone (for my taste at least)
- I own the very similar PC350, they are super comfortable for me as I can wear them the whole day with zero issues
If you want to pay less:
Steelseries Siberia V2 $67
- classic semi-budget gamer's headset