A good headphone can probably still outperform a speaker system. The tradeoff is that you have to wear a headphone. In my case, I just hate them. It's just more pleasant for me to listen from speakers, despite the fidelity tradeoff.
I never really liked wearing headphones as well. I've setup my room such that I can use the big stereo speakers plus a decent mic (Samson Go Mic) for voice chats.
However, Sennheiser HD650 are a pleasure to wear. Even for longer periods of time. I use them with a bluetooth+USB DAC/amp (Fiio Q5; outdated) and a short cable; so I'm pretty flexible how I can use them.
There's also the fact that when you really get "into" the music and start moving your head, there are basically two scenarios: you either get the "hum" of the headphones moving on your ears, or the headphones stay put but the clamp is so tight that you can't stand them for more than 10 minutes.
Headphones are excellent, but I find I have a different experience with headphones compared to music coming out of speakers. Sometimes I prefer one over the other.