I don't use very expensive headphone. I use Beyerdynamic DT250. The first I look is the good seal to my ear, so I can hear more without going loud. AT M50 and above all are good for me. The DT 250 got low impedance, not good for portable but ok with most of the headphone amp. This model is more rich than higher model.You could say a bit less accurate. It is a bit less high compare to most close back headphone. Most of studio headphone are very clear in high, but I will find them fatigue after long listening. It is not best in sound, but definitely you can endue the longest. The best headphone is using electrostatic driver, very clear sound and yet easy to listen.
The best solution is using in ear. But you must get a very good seal in your ear. You could hear deeper and better bass definition than headphone. The rest of the frequency is very well define. You crank up much lower volume to listen all. You need to do customise ear plug to obtain best result for in-ear phone. Many brand in sub $300 class is good enough in my opinion.