At the low price point, you can get a digital audio player with a human-ears-perfect DAC and a human-ears-perfect amplifier for under $100, that will feed headphones of sufficient quality for between $50 and $200 depending on your criteria.
If it doesn't need to be portable, that's certainly a good way to go. Note that the Allo Boss2 gets you everything except an amplifier and speakers, incluyding a Pi4, assembled, in a nice case, for $185. You might like to run Owntone (formerly forked-daapd) on whatever machine holds your storage - or anything else; the Pi can mount your storage via NFS or CIFS or basically anything else.
You can have a look at https://www.audiosciencereview.com/forum/index.php and its reviews section. This is a good site in general (there are others) if you are interested in audio reproduction topics and reviews that are supported by science, not flowery prose of reviews in so called HiFi magazines and sites.
(And it's all portable.)