Best Headphone system under $1000???


Hi all,
I've been a 2 channel audiophile for 30+ years, and I'm ready to liquidate the big system and simplify.
I'm interested in finding a really nice set of headphones and a headphone amp, to pair with my DAC and MacBook based Tidal streaming source.

Interested in staying within the $1000 range (or under) for headphones and a dedicated headphone amp/preamp.
As far as tastes go, I prefer a "musical sound" to the more hyper detailed hifi/neutral sound. I enjoy jazz, funk and R&B, classic rock, and some classical, so I'm hoping for a headphone system that is slightly warm and has good soundstaging.

For reference, my big system has Vandersteen 2CE Sig 2s, Odyssey Kismet amp, and a nice 6SN7 tube preamp from JE Labs. I like the full, colorful, dynamic sound of this rig and hope I can replicate it in a headphone set up. 

Any recommendations would be very much appreciated!
Thanks!
Lincoln
lincnabby

Showing 1 response by lincnabby

Wow guys! I truly value all of your feedback! 
I’m definitely checking out all of the possibilities that are available on Massdrop. It seems like a great place for dipping my toe in the headfi pool. 
The Focal cans and the Sennheisers were two that I was looking at closely. 
James63- I especially appreciate your way of comparing different cans to speakers I’m familiar with. My initial impulse was to get Massdrop HD6xx and pair them with the Massdrop Cavalli CTH headphone tube amp. Has anyone heard this combo?
Net cost for above would be $550. 
However, the Elear and Elex has piqued my interest. Especially if I could drive them with my iPhone X when I want to be portable. 
I have a decent DAC already- MHDT Stockholm 2. 
Any further advice or suggestions is most welcome.