Headphone suggestions needed

You should try Cooler Microsoft Surface Headset. Have best call quality even on outdoors.

Can’t beat the Akg closed back but open sounding k550’s excellent headphones, although you would have to settle for mk2 version. Shure makes two nice options in the closed back 1540’s and open back 1840’s. Also, now discontinued Audioquest nighthawk and nightowls. AQ got out of the headphone business, but these two were highly regarded headphones. As for an Amp to drive them, I like the Graham Slee Novo or the solo. I’ve had those aforementioned AKG k550’s for years now, they are my go to headphone, comfortable and non fatiguing sound, with plenty of detail and sound like an open back, but no sound leakage whatsoever. I own the Graham slee novo headphone Amp and it drives just about anything. Not sure why people always mention a dac to go with headphones, as the dac I use, the Border Patrol dac, is used within the system for cd playback, connected to a Cyrus cdt. Unless you are just doing a desktop dedicated headphone only set up, then I guess you would need a dac, idk. When I need to listen to headphones, I use the Novo, as I can play all sources through it, as it is a daisy chain style Amp. It is unique In this respect. I can listen to my cd’s, turntable, cassettes, fm tuner, and streamed music through my Novo, all I have to do is change the source selector on my integrated amp.

My suggestions would be:

-Meze 99 Classics

-HiFi Man 400i

-Grado RS1e

-Audioquest Nighthawk or Nightowl (If you can find them, discontinued)

The above mentioned headphones are used with a Cary HH-1 tube headphone amp.

I use a Synthesis 41DC+ integrated tube amp (ECL82/6BM8 in a Single Ended 2W class A), source is USB from a PC usually running Tidal using CD Lossless quality. My headphones are the Audeze LCD-2. I am very happy with this arrangement. It's clear and huge, and has a ton of bass for the clarity. I also run low capacitance litz cables and an IsoTek Evo 3 power conditioner. 

I do like, in general, how magnetic planers have sounded with my tube amp more than any dynamic but I can't speak to many headphones in the $1000 price range.

It seems the LCD-2 (70 ohm, >100mW Min, >250mW recommended ) would match the impedance/power output of your amp (30-600 Ohms; 200mW/300 ohms, 300mW/30 ohms), which should give you at least the 250mW into 70 ohms that the LCD-2 recommends. I think you should give them a try. It's so far my favorite headphone and they are very comfortable. But amps are all different, your mileage may vary. But it should be a contender. It really blew away my Senn 6XX in every way and you see how much praise those get.

I have loved how HiFiman and Grado pair with the Synthesis as well, at a variety of levels. The Arya should work if you can find it in your price range, and for Grado the RS1x. If you don't see recommended power rating, look for over 90 db sensitivity.

The Synthesis uses a Asahi Kasei AK4495S DAC chip, not that that tells you much. Sorry I can't be more help for the DAC.