The comparison isn't between closed and open cans though. It's closed cans vs IEMs and desktop powered speakers (Vanatoos). Is there an enjoyable difference?
Just going between closed cans and IEMs I've owned headphones have worse isolation, more "there"-ness (probably cup reverb or something), and are far more comfortable. Quality of components, design, and voicing can change the experience a lot.
No headphones or IEMs will be able to replicate the visceral experience of speakers since it's all on your head, or in your ears, as opposed to being felt by your entire body.
A good pair of open backs can have smoother, more even treble (esp. the transition from mids to treble) than a similar closed, with better instrument separation and an enhanced sense of spatial boundaries. Closed headphones (and many IEMs) have a bit of a bass boost compared to what you'll get with open-back. Depends on what your sonic priorities are.
Next foolish help-me-live-my- life question. I've got the GO V2A - should I get the MD Senn 6xx for 220 or the ZMF Aeolus for 1200? Context: I love the JVC FD01 for their tactility, balance and tonal rightiousness.
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