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
Very interesting discussion. I’m rather new to phones (speaker guy) and just bought the Beyer DT 990 Pro with the Topping DX3 Pro dac and amp. After googling and for a start. I like it but would be fine to have your opinions. I also have the AKG (Quincy) 701 which have no warm at all. Just a precise working tool maybe. I find the DT 990 a little smaller in soundstage and a little less emphasis on the mids than the AKG 701. The AKG can easily be a bit too much for long-time listening. The DT990 for me non-fatiguing but still very clear and well-balanced. And very very comfortable. However, based on this short experience headphones will never ever be instead of speakers :-) But is a fine reference for evaluating your speaker sound.
@gosta

https://www.rtings.com/headphones/tools/compare/akg-k701-vs-beyerdynamic-dt-990-pro/326/329?usage=49...

They indeed show less outout at around 1kHz and a wider “soundstage” for the AKG. Take note that their definition of imaging and soundstage are not like the definitions for speakers, they use “imaging” in regards to reproducing what’s in the track and “soundstage” in regards to emulating listening to stereo loudspeakers in a room. They rate the AKG as more comfortable (less clamping force), but do also show the Beyerdynamic as being more breathable, which also factors into comfort. 
Actually I got the Q701 so they have the same rating as the Dt990 but I can assure you they are very different! Didn't know there's so much fuzz with the upper registers in phones.
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.