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I'm glad this amp is getting some action here. I got one in a previous drop and enjoy it very much. It's very organic and more natural sounding than my opamp based portable amps.
As stated, it is a warm and musical sounding amp, so proper matching with IEMs or phones is in order.
It can sound great, but when paired with warm sounding IEMs, can sound too warm and mushy. It'll probably do best with more neutral or clear sounding IEMs for a nice balance, IMO.
@K.T.N Are the Hifiman (560) or the Beyerdynamic phones (T51i) considered neutral or clear sounding?
Sago, unfortunately I haven't used those phones on the Picollo, so can't advise you on how well those work. Perhaps someone else who's tried the combo can chime in.
I actually use only IEMs currently for portable listening. So I don't have too much advice about how well specific full size headphones might sound on the Picollo.
I can say in IEMs, I like the Fidue A83 and the Audeo PFE232 (which is also dropping currently) with the Picollo, as well as that one that dropped here a while ago - a fairly unknown Chinese brand that features customizable tubes to tune the bass and midrange. I forget the name of that one, but it sounds great with the Picollo as well.
My recommendation is just a general suggestion based on the tonal balance of the Picollo. It also reflects what I found after trying a number of my own IEMs.
All phones and IEMs have unique electrical characteristics outside of tonal quality that may or may not allow them to work well with the Picollo. So short of having tried a specific combination, it's hard to say whether it will sound good.
Good luck on your search!