rv, since circumstances require that you use headphones at certain times, you owe it to yourself to try a really good headphones set up. Two very different experiences, headphones/speakers. Overall, I prefer listening on my speakers, but those times when I want my listening to be private headphones are great. Still other times I want the, what is for me, the very intimate and immersive experience of headphone listening. However, while I agree that relatively inexpensive headphones can sound good, it is not until one experiences what great headphones can do that things get really interesting.
mahgister makes a great point, as usual, about the benefits of acoustic control of the listening room, but in doing so he also explains why headphone listening can be so good - room effects are completely taken out of the equation. It is for this reason that I think it is not a matter of “better” or “worse”. If one does not object to the “sound inside one’s head” effect and can make the adjustment away from the usual “large soundstage in the room and in front”, an excellent headphone setup can compare very favorably and even surpass just about any loudspeaker in most audiophilic parameters with the possible exception of the visceral impact of low frequencies.
I own Stax Lambda Pro electrostatic headphones with the T1 dedicated tube driver and the sound is fabulous. Amazing detail, tonal truthfulness, dynamics and very articulate and extended bass lacking only that visceral “whole body” feeling. Stax, because of their design do a pretty good job of moving the “soundstage”, while still “inside your head”, to somewhat in front of your head. This is why Stax refers to them as “ear speakers”.
Highly recommended!