I’ve gone back and forth on this for ages. Actually got my start in audio with hi-fi headphones (Sennheiser HD580), and I think that imparted in me a strong requirement for "coherent" sounding speakers - because headphones offer (with few exceptions) a single-driver full range sound. This is why I’ve been exclusively a Tannoy DC user for the past 20 years (phase coherent point-source DC drivers). I’ve never liked many of those uber-expensive behemoth multi-driver speakers. In fact with some of the other high-end brands I do like, I tend to prefer their smaller models a little down from the flagships.
Anyways, headphones CAN be highly enjoyable to me, but it’s a rather hit or miss affair. I have to be in the right "mood" for them. Some days I just can’t be bothered. Tannoys are simply more engaging day to day, and the visceral impact of speakers is a big part of that.
When I do listen to headphone now, my favored set is the electrostatic ES Lab (Hong Kong) ES-1a or ES2a, with a really good e-stat tube headphone amplifier: currently using a Blue Hawaii SE, though there are better amps out there like DIY T2 and Megatron. These ES Labs headphones have a more natural voicing than modern Stax, and a bigger soundstage ("head" stage) due to their larger drivers & cups. I still do like Stax, but the ES Labs are now better IMO. Tubes are also very necessary to impart a natural voice. Dynamic (moving coil) headphones are either far too colored or too boring, and frankly their listening fatigue is AWFUL. E-stat headphones are comparatively smooth as silk and won’t hurt unless you’re listening WAY too loud - which is actually hard to do because of their insane voltage drive requirements!
Anyways, when I’m in the mood, this ES setup is pure ear-candy - BUT if I’m able to run my Tannoys I’d still probably rather just do that :) These headphones are really nice though; way WAY better sounding than most.
For a few months my VAC 450S amp was out of commission, and it really took the Tannoys down a couple pegs :( I tried switching to headphones and that was great for a few days, but then I lost the mood and basically didn't do much listening since then. This week the VAC is finally back, thank god! What a difference...

