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!
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... 
For those trying out grados for the first time the Grado PS500e is easily their best IMO. It has all the details of the others or more but softens the 2k midrange spike and has a lesser more balanced treble. Makes for a relatively warmer Grado (still bright). Sadly I had to get two pairs to get one with good driver matching. Order from some somewhere you can return them...

I have owned/used the following grados and choose the PS500e.

PS1000e (scooped out mids, they call it soundstage, I call it messed up tonal balance)

PS500e (good, light/fast sounding and punchy like good monitors, a little bright still, I love the close vocals).

GH1 (a lot like the PS500e but more colored mids, you can hear the wood in the bass for better or worse)

GS2000e (uhm no, really bad, just no, ear tweeters, funky soundstage)

RS2e (brighter and less bass than the PS500e, small spike at 2k)

RS1e (I don’t really rember these...)

RS325(pretty bright, probably the brightest Grado I owned, ok other wise)

RS225e (light on bass, more open mids from the models down, a poor mans RS1/2)

RS80e (Best buy, most of the Grado sound for under $100)

RS60e (warmer of the grados. Tuned like the PS500e but less open and detailed acrossed the whole frequency range.

This is fun- haven't created a thread with this many responses in quite awhile. I'm still waiting on my little Atom amp and in the meantime, beginning to surf the web looking at IEMs too. 

Anyone have recommendations for an IEM that leans more toward the warm side of neutral and has exceptional sound staging/imaging?

I might explore this realm of headphonia too, but probably wouldn't want to spend more than $300
Update- with the Focal Elex, the JDS Atom amp, and my MHDT Stockholm 2 DAC, things are sounding pretty damn good. I do have a VD Nite II power cord running into the DAC and a pretty high $ IC from amp to DAC (stupid considering cost of headphones and amp?) but I’d say the PRAT, detail, and immersive soundstage rivals and in some ways exceeds my full size rig. 
Hopefully, I can manage to just relax and enjoy the tunes for awhile!