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
Headphones just like speakers all sound very different from each other. 

IMO I would tell you headphones are better than speakers for all things other than visceral impact and sound stage. Do I enjoy headphones more? No I value sound stage too and impact too much. 

But some of these new headphones really are special. Keep in mind that a pair of headphones is pretty much a microphone in revirse. One drive, no crossover, controlled environment, crazy efficient, less box/housing noise, etc. 

some headphones are a total mess though (very colored) and I think just now in the last few years with all the portable music craze we are starting to see real improvements in the highend headphone market. I would argue high-end headphones are just now starting to be made. 

For years you bought sennhisers or grados for the most part. Now you have startups pushing limits and big power houses like Focal pushing the state of the art. 

Focal’s first try pretty much equaled or bettered (IMO) what was out in the passed. It will be interesting to see how they push forward over the next few years. 

@gosta 
 
For Rtings, never look at category ratings, look at each specific test. The AKG’s have much better soundstage, but they also have less bass, so their combined rating is similar.
I use phones for late night reading mostly, and after wearing out some very old Grado SR60s (I like the Grado "house sound") I replaced them with SR80s...improvement for sure...running an old iPhone that still connects with the net as a source. I recently bought a couple of Schiit Magni 3 amps (for bedroom and main system) and Grado SR325e aluminum body phones...amazing SQ that surprised me really, and they sounded great immediately with a world of difference over the el cheapo 60s and 80s. Found some "G" (large over-ear pads with hole in the middle, sold with top of Grado line phones, and 50 bucks from Grado) ear pad clones for around 12 bucks shipped from China...very comfy at least compared to stock ear pads.
Headphones are definitely a personal taste thing .   Hadn't used phones in years and stopped into Q Audio in Boston one day at lunch.  Tried on several Grado models from the 125s to the GS2000 and bought a pair of RS2e that day.  
Tried the Focal Elear and Focal Clear today in a shop and fell to sleep. Moved to the Sennheiser HD820 and woke up. Sounded like
my near-fields but a little thin and less dynamic. Very good separation though. Not too much impressed for that kind of money. They all need a special amp. The one used was the Sennheiser HDV 820. Beyer DT990 Pro seems like a good value...