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 hear the Bottlehead’s are awesome, but you are talking about much more $$ and you’ll have to build it from the kit.
For $99 nothing is better than JDS Labs Atom (well, the monoprice Liquid Spark is nearly identical to the Atom sound quality wise, so they say) so you can’t go wrong either way. I know the Schiit Magni for $99 is also a tremendous deal, but I hear the sound quality may not quite be up to par with the Atom or the liquid spark. I love Schiit Audio overall though, great products.
I’m now in a bit of a conundrum. I’ll be getting the Focal Elex cans soon, and also have the Senn HD6XX. Wondering if I should just be frugal and get the JDS Labs Atom amp for starters to listen to both?
Since I don’t have the Elex yet, I’m not certain, but imagine they’ll be the ones I keep. I like the liquid sound of tubes and have a tube based DAC. Do you think the Atom and Elex with tube DAC will suffice?
Ultimatley, I know my ears will be the final judge. Still more opinions are welcomed. 
Also- it sounds like the BH Crack might not match well with the more efficient Elex. Does that sound correct? 
I’m such a newbie to head-fi...
I would get the JDS labs first and call it good unless you can think of a reason to get something different. It should drive both headphones fantastically.
You can get more ideas from reddit
https://www.reddit.com/r/headphones

If you want to try more headphones I recommend Beyer Dynamics. Dt1990 is said to be very good and details. I have the Amiron Home which are a bit softer. They are both probably better than your HD6xx but not as good as the Elex.