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

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I was able to buy Cary HH-1 and Sennheiser HD 700 for less than $1,000 in total, each new from manufacturer just by keeping an eye out and jumping when the opportunity arose. Cary had a flash sale on the HH-1 for Christmas 2017...

I am quite impressed with the combination. When they died, I replaced the stock Electro-Harmonix 6922EH with Genalex -Gold Lion E88CC/6922 for marginal improvement in tonal qualities.

Most people find these Sennheisers too bright, but this amp curbs that in just the right way. The sound is lively, tight bass, revealing and seemingly neutral while still having that tubey je ne sais quoi.