@astr0 Generally, I don’t use headphones when listening to classical, or other music. Occasionally I will, but more often than not, I use my 2.2 hifi system for music.
However, when I do use headphones I will use the Sennheiser HD650 or @ZeosPantera Eris headphones. I never use IEMS. I have a couple pair of them, but I don’t use them because I don’t like the feeling of them jammed into my ears.
@astr0 @TimpTim44 is speaking some wisdom. Truth be told, like @SandboxGeneral I enjoy classical the most on speakers. But on those occasions when headphones are the appropriate choice, I have been using the SJY Horizon Closed Carbon headphone, driven by a speaker amp, the SMSL DA-9. This pairing is presenting classical music to me in a way I’ve not heard it before. It puts you center stage, about 5-6 rows back. Simply spectacular. That said, I still prefer speakers!
As for IEMs, I don’t have many sets, but the Mega5est does a fine job. If memory serves, The Pula PA02 was very nice as well. Well now I am gonna have to pull them out this weekend and find out!
Hope that helps. Enjoy the music. 
Speaking of enjoying the music, I found this wonderful video this last weekend. This is my first time listening to Maya Oganyan play. Just WOW. Enjoyed on the bedroom system, of course. Love classical on that old system!
That piano creates such a beautiful sound. I had not seen one until this video.
Easily one of the most extraordinary piece of music ever written. And Wow this production.
This bit here:
I’ve done it again! I have found a piece of music that grabbed me for whatever reason and then went on a search to find my favorite performance. I’ve been at it since last night! This time it’s Beethoven’s Piano Concerto No.3, op. 37. Turns out there are a vast number of players that have performed this piece, so it’s been fun listening to various interpretations etc. So far, I have come back to this one as my potential favorite.
This is a great record, btw. I may have to add it to my collection.
