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
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.
I am using a pair Grado RS2e with a Rupert Neve RNHP headphone amp and it is a great sounding combo.
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.