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
This is fun- haven't created a thread with this many responses in quite awhile. I'm still waiting on my little Atom amp and in the meantime, beginning to surf the web looking at IEMs too. 

Anyone have recommendations for an IEM that leans more toward the warm side of neutral and has exceptional sound staging/imaging?

I might explore this realm of headphonia too, but probably wouldn't want to spend more than $300
Update- with the Focal Elex, the JDS Atom amp, and my MHDT Stockholm 2 DAC, things are sounding pretty damn good. I do have a VD Nite II power cord running into the DAC and a pretty high $ IC from amp to DAC (stupid considering cost of headphones and amp?) but I’d say the PRAT, detail, and immersive soundstage rivals and in some ways exceeds my full size rig. 
Hopefully, I can manage to just relax and enjoy the tunes for awhile!
Update-
I’m officially on the head-fi crazy train now. 
I purchased a Woo Audio WA-6 amp to replace the Atom, and have enjoyed a fairly significant improvement with the Focal Elex cans. In my former 2 channel system I really loved my 6SN7 & 5ar4 based tube preamp, and the Woo uses these same tubes.
 If any of you out there have specific tube recommendations for the WA-6, please share. 

Also, curious if anyone with the Focal Elex has dabbled with cable upgrades?
it may be a waste of money, but I definitely fall into the “believer” category for audible improvements with speaker and power cord upgrades. 
Thank you for any advice. 
I had the Woo Audio headphone amp with two Sylvania Bad Boys and one 40s Tung Sol rectifier Tube, I also suggest you get Herbies dampers for all tubes. 
Would recommend braided (kind of following Kimber cable's philosophy) and look for OCC copper (ohno cast single crystal copper) possibly sliver clad, as well. Enjoy the crazy train! We now grant you an official audiophile carrying card...