I feel more like headphones are to HiFi, as watching porn is to sex. Listening on headphones is better than nothing. But at the same time, it can be shocking how much of an improvement speakers bring to your enjoyment of music compared to headphones.
IF you have the requirements to enjoy well designed, positioned and measured in speakers, yes. Speakers are preferable.
For that to apply you need your own house though, preferably with an optimized and treated room solely dedicated to audio. If you don't have one, the question whether the Neighbor may be disturbed by your music or not will always be in your head unless you turn the SPL down to very low levels, which starts to mess with the spectral balance of the content. Not to mention quiet music being even further away from the "live music event" than headphone listening at the "appropriate" SPL.
Personally I agree with
@raistlin65 : Listening to cans vs listening to speakers are simply two different experiences with different points of merit and weakness. For me, the biggest benefit is carefree enjoyment. I do not have to think about other people when I put on my Clear and can focus all of my attention on the music. The biggest benefit of my speakers are imaging and not having to wear sth. on my head.
For the record: I have never attended a live event, nor do I ever intend to do so. So many people crammed into the same place would just make me run away within seconds. So my view is probably less biased than yours, since I do not try to re-create any particular experience. I can only say that neither headphones nor speakers stand any chance at all to recreate what I feel when I sit down at the grand piano in my music school. Alas technology simply isn't there yet.