For me, it depends on the mood I'm in. If I want to do any critical listening, I would much rather use my Grado HP-1s than my speakers, but there are some recordings that just need to be played over good speakers to get the full effect of the music. Then of course, there are binaural recordings which can sound better than any stereo recording played through speakers. I also like speakers because headphones are very anti-social items; You can't share the sound of music with people through headphones (barring Grados played at obscene volumes). I listen to my headphones more often than my speakers though. The moral of the story, each has their own benefits for their distinct uses.
I go back and forth. I like my horn speakers when I'm going for dynamics and the full body effect and headphones when I want to pull out the details from a recording. It's kind of interesting to play a CD or LP on the speaks and then play again with the headphones, you get a whole different kind of presentation. Lately the headphones are getting more exercise.
After a while you just develop a preference, and a speaker based setup to rival the clarity and tonality and range of our headphones would be obscenely expensive.
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