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
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... 
In regards to your question about cables, I have Focal Elex and Sony MDR-Z1R headphones, which both have the same connectors.  I've used a few different cables, mostly mid-grade to inexpensive cables. 

To me, there is not a noticeable difference between cables, which is also my experience with interconnects, speaker cables, etc. 

I buy cables for fit and finish, length, different connectors (balanced, single-ended), not for sound quality.  Which isn't to say that there aren't differences in sound quality, but that unless I A/B them back and forth repeatedly, there aren't differences noticeable enough (to me - your hearing may be more sensitive) to make me prefer one cable over another.  
Geoffkait- I’m actually leaning toward vintage Sylvanias. I had Shuguang Black Treasure CV181z tubes, and they surpassed NOS with my old pre, but they’re very pricey and I’m wondering if it’s as critical in this Woo amp. I bought it used and it came with a Sophia Princess 274b rectifier, which is pretty well regarded, but considering a Mullard GZ34in that spot. Might call Andy at VTS. 

Bstatmeiser and big_greg:
Appreciate thoughts on cable...
I was actually looking at litz braided upocc cable from a company called Dyson Audio. 
About $135 for a 2 meter. 
I can definitely hear clear differences between ICs, PCs, and speaker cable, but it does require lots of A/B tests and tweaking. For me, that’s part of the fun, but I respect those who don’t hear it. They’re saving lots of money!
Once I empty more of my wallet, I will post again with impressions!😀

How would you compare the Audeze LCD 2 against the Focal Elex headphones? They both seem to get good reviews within the price range