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
One of the great things about the HD-6XX is that since the HD-600/650 have been around forever there are a lot of aftermarket accessories for them - cables, earpads, etc.  Putting some nice earpads on mine made them a lot more comfortable.  I didn't notice a huge difference in sound quality as some claim, but the comfort level went up.  You may need to purchase a plate, depending on which earpads you get.  Check out modhouseaudio.com for those.  I don't remember which earpads I bought, but there are a number of choices out there including Dekoni, ZMF, Brainwavs, and more.
Thanks again guys!
My impulse control failed miserably as I just bought a pair of the 6xx’s and also saw a decent deal today for the Focal Elex’s, so I made an offer. It will be fun to compare both. 

Regarding amps, I’m planning on checking out the JDS Labs recommendation. Is this just a good match with the Sennheisers or would it mate well with the Focals too?
I understand that the Focals are more efficient. 
Also- any opinions on the Bottlehead Crack with Speedball mod kit? 
Going DIY to save on a possibly good amp sounds like fun. But not sure about impedance matching. So much to learn. 
Hopefully with all of your help I will avoid potentially expensive mistakes. 
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.