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RE: Travel and Music

Ear buds are really the most compact solution, but if you don't like 'em, well, you don't like 'em.

I use a Sony NWZ-A17 DAP. It's so small and light, it's almost invisible. And it sounds terrific. No DAC needed, no using up my phone battery, it's battery life is tremendous. Sony uses some kind of processing (DSEE?) to make lower res files sound great. It also plays HiRes files, and I play my 24/192 LP rips on it. Downside is the user interface isn't very friendly (no touchscreen), but manageable.
https://www.amazon.com/Sony-Walkman-NWZA17SLV-Hi-Res-Digital/dp/B00OCJRX8C/ref=sr_1_1?s=electronics&ie=UTF8&qid=1487256739&sr=1-1&keywords=sony+nwz-a17

I use Shure 535 IEM's, but like you, find them irritating after awhile, even with the Comply tips. The on-ear cans I use are the Beyer 1350's. They are durable and light, and isolate quite well for on ears IMHO. Another portable on ear to consider is the Senn HD25.
https://www.amazon.com/Beyerdynamic-DT-1350-80-Supraaural-Monitoring-Applications/dp/B004QMH8KI/ref=sr_1_1?s=electronics&ie=UTF8&qid=1487256826&sr=1-1&keywords=beyerdynamic+1350

Cost is well above $140, another downside.


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