Best portable headphones and DAC

The operative word is PORTABLE.  I like my current set-up (which consists of an AQ red dragonfly and a folding pair of sennheiser headphones.) but I,m wondering if there is anything better out there.  I also have a chord mojo but I,m not sure I would categorize that as portable.  It mAy be fine for taking on a flights but it's too heavy for walks or bringing to a health club , IMO.  I'm debating about upgrading the dragonfly to "cobalt".  The reviews are mixed as to whether it's worth it if you already own the "red".
Sennheiser HD-580 or 600. I don't know if that's too big for your purpose, but upper end Senns sound heavenly for me, with the right source and headphone amp.

You mention headphones.  Just wondering if IEM were considered for even more portability.  There are several great ones for $200+.
Celtic66 (Boston Celtics fan I wonder):  re IEM's:  too many trips to the emergency room to remove the ear tips (unfortunately, I'm serious) that were lodged in my ear canal.  My wife was not amused.  I found that to get the best sound the ear tips have to be completely inserted in the canal and for that reason, i started using a lightweight headphones.
I have the Dragonfly Red and have listened to the Cobalt and the Chord Mojo. The Cobalt is smoother. My thought is that the added punchiness of the Red might actually work better for mobile usage. One way to increase the smoothness of the Red while retaining the punchiness of the sound is to add an AQ Jitterbug.
I like Dragonfly Cobalt a lot. Better than both Red and Black, both with in-ear headphones and my Grado RS-1.
Inna, I did upgrade my dragonfly from red to cobalt.  I purchased an open box IEM (Fiios FH7) as I gave up the search for a portable headphone which would be an upgrade to my cheap Sennheiser (PX100?) phones that I,ve been using the last 10 years.  That said, I did consider the Grado,s (325 and 225, I believe).  While I would concede that these have a smaller profile (and assumed to be lighter as well) I,m not sure I would categorize these as portable.

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