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
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
How would you compare the Audeze LCD 2 against the Focal Elex headphones?
They are both excellent headphones.  The LCD 2 is going to have more bass and be a little more "rolled off" at the high end (the Audeze "house sound").  They still provide good detail and excel in the mid-range.  The Elex is going to be a little more neutral throughout the frequency range and I find them more comfortable to wear.  Which isn't to say that the Elex lack bass or that the LCD 2 is uncomfortable.  The Elex has good bass response and maybe a little more "realistic".  One of the things I like about Audeze is they come with really nice earpads and are comfortable from that standpoint, but they are a little on the heavy side.

I suggest checking out Headfi and Innerfidelity for in-depth reviews of both.
Don’t know why but I went all in with a headphone setup just recently. I’m a redbook CD guy using Sonos and that’s not going to change - too darned convenient for me.

Sonos > Benchmark DAC3 B (DAC, only - no volume / amp / headphone jack / ..) > Woo Audio WA2 > Sennheiser HD800S.

Kimber Silver analogs and digital cable.

It’s been awhile since I’ve been ’taken someplace new’ with music.

(Also considered the Chord Qutest.  Got turned off by the 'filters'.  I wanted as pure a signal to the tubes, as possible.  I contacted Benchmark and they said to not worry about jitter - the Benchmark will take care of that.  I had told them I have an Empirical Audio PaceCar 2 I could put into the mix).