Best Headphone system under $1000???

Grado RS-1s with their battery powered pre-amp.

Enjoy a great hobby, here’s my two cents...

I currently have the HiFiman Anandas, they are right at the 1k price point.  They are huge, but light weight.  Sound is amazing, best I’ve owned.  They can run easily off a phone but as with most, sound better with better DACs/Amps.

I’ve had Audeze LCD-X (way too heavy, ok sound), the Massdrop HD-6xx (ok but un-dynamic sound, no-go with a phone), and still own as a back-up Audioquest Nightowls, which sound great but have been discontinued as Audioquest got out of the headphone business.  They are a great used bargain if you can find them, usually $150.00 to $200.00.

Just for info, I use a Mytek Brooklyn DAC+, which is a DAC/Amp combo, and listen through a balanced set-up.  Source is a Dell Desktop Windows 10 with Tidal, and more recently Qobuz, as my music sources, both at the highest quality available.  I have a LG V30+ Android phone and an Audioquest Dragonfly DAC/Amp that I sometimes use for late night listening, often wirelessly with Bowers and Wilkens PX noise cancelling headphones.  The phone transmits the high quality Apt-X HD version of Bluetooth, which the B&W headphones accept.  Very happy with the SQ of the headphones, but they could use a bit bigger earpieces for my big ears!

https://www.ebay.com/i/292882883497?chn=ps&ul_ref=https%253A%252F%252Frover.ebay.com%252Frover%2...

Meze 99 Classics Walnut Silver Headphones (Silver Black) https://www.amazon.com/dp/B01EJMYOHO/ref=cm_sw_r_cp_api_i_Wp0GCb5HW0C7M

The amp in the previous post would be a good buy. I have the M1 HPAP and it's a solid performer. It's only good for connecting source components though, the USB is not very good.