Your oldest gear?

@ghdprentice no- not those. Mine were light open backed and a pleasure to wear 

The Koss head crusher.
 

I think the most affordable, nicest sounding, but most uncomfortable Koss headphones were the 1970’s PRO 4AA’s.
 

As l say, they sounded brilliant, and they completely isolated you from the outside world. Closed cup and heavy, and had outer ear crushing leather pads. It was okay for the first side of a record, but after that your ears started hurting and sweating. When you took them off your outer ears felt as flat as pan cakes.

Had the Koss PRO 4AAs and yes they were very uncomfortable. The AKG K240 was much more comfortable and better sounding IMHO. My oldest piece is a NAD 4150 Tuner, quite a disappointment after owning the superb NAD 3140 integrated amp.  Not sure why I kept the tuner all these years. I also kept my Kyocera A-710 integrated amp and still use it in a second system.  It sounds great to this day.

Stupid perfectionist that I was, I chose the Koss Pro4A back in the 70s instead of the lightweight Sennheiser foam model.  The Sennheiser floated comfortably on the ear but did not seal out external sounds so well, allowing for a less pure sonic experience.  I could not wear the Koss for long and did not use them much.  Years later, I paid up for a pair of Stax electrostatics and kept them until the foam rotted away.  Just walking around with Airpods these days.

I’m a big believer in FULL FEATURED Preamps, often all manual. I use a Chase Remote Line Controller for Remote Volume, directly or optionally thru a tape/processor loop. Mute is nice also. 

what do you do for remote volume? 

Happily, it has Remote BALANCE also, what a treat that is.