Personally 2 channel audio is my priority. My main system is so far superior to any headphone setup i've heard, and I live by myself, so I can listen to music at reasonable levels whenever I like. But if you co-habitate, or live in an attached apartment, having the option to connect headphones can be an advantage. Leben integrated amps have a very good headphone amp. And the headphone amp in Accuphase integrateds is good also.
I gather from the definition in Wikipedia that the name was derived from the use of headsets in telecommunications and radio, and became the generic term for audio cans as well.
Seems like a question you should be asking yourself.
If you do not have neighbors, or others you would disturb, then speaker listening is my preference. If you have limitations because you may disturb others, then headphones may be a good option.
I almost always opt for listening with speakers. It is a much more visceral experience. Headphones only energise the teaspoon of air in your ear canal, speakers energise the air in the entire room.
While I usually turn to my two channel loudspeaker setup, there are times I turn towards a relatively high end headphone rig. I think of them more as “different” than “ranked” - and very personal mood related.