I have owned both. I used to own what some would call the best headphone available.the abyss AB-1266 PHI TC with a formula s, powerman and dCS Bartok. I upgraded my speakers from Magico S1mkII to a pair of Rockport Atria II with pair of JL F110v2 subs. After that I sold my Abyss and headphone amp. They got no use after I upgraded the speakers. There is just something about a great speaker system that headphones can't match. I still have focal clears and noble kahns with an sp1000 for late night listening.
It does cost a lot more to get the same level of performance from speakers though.