Headphones

really expensive audio is like really expensive clothing. the reason the price is higher is usually something besides the core functionality of the product in question.

and keeping along that path, fit and synergy are more important than the mindset that thing over there costs more so it has to be better... that's not true with jeans, and it's not true with IEMs or amps etc.
IMHO you should go into all audio purchases with the idea that what you're getting is going to sound different, not "better" - especially not if you're already firmly in the mid-fi game and spending hundreds on gear.