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
Big_greg

Agreed and good point. I think a lot of classical guys would appreciate the HD650/HD6XX and they are a steel. They were $350 10 years ago and they might even be cheaper now. I wish the same could be said about the speaker market prices...
Update. 
I found a pair of Senn 6xx on my local craigslist for $160. I think I’ll give them a try. Also will probably try out the Cavalli CTH from Massdrop for $299. 
I’m a tweaker by nature so this will probably end up being just the beginning of experimentation. 
I wish I could find the Focal Elex somewhere used. Gotta sell some other stuff before i start dropping larger amounts of cash. 
I’ll update you all on this thread as to my impressions on this first combo. 
Thanks again to all!
@lincnabby

That Massdrop tube amp is decent, but the JDS Labs Atom is better and cheaper. It may or may not be audible, but that Massdrop tube amp leaks power supply noise (multiples of 60Hz), so a power conditioner with noise filtration may be warrented, whereas the JDS Labs Atom does not have this issue.
Lincnabby,

You will like the HD6XX.They may not wow you at first but they are excellent with no major issues that so many other headphones have.

I am always interested to hear the perspective of headphones from someone into speakers.

I started with headphones in college and moved to speakers for about 15 years. I tried to go back to headphones after owning a good speaker system... I almost pulled it off but in the end I miss the impact/slam of the speakers. Most people miss the sound-stage.

I had a good two year stretch where I just used headphones (by choice) 90% of the time but now I am back to speakers most of the time and only use headphones if the kiddo is sitting with me (she often does) in my audio room.

Headphones will show you what is wrong with your speaker system and your speaker system will show you what you are missing with the headphones.