Like everybody I started with cheap headphones, but grew a little collection and some over time. I think I got the big soft red open headphones from a competition, and discovered they served me well for DJing, being able to hear the room over the music depending on the volume.
For gaming I got the classic HyperX Cloud II Headset. In my time in Berlin I stumbled upon headphones by Degauss Labs, soon ordered the Bluetooth Vice and later their flagship Twelve Drivers at a discount. Their modularity enticed me, and they served me well over the years. While the MMCX connector is not suitable for switching between different cables frequently, it does allow you to exchange just the cable when it is broken, keeping the expensive earpieces.
After the cheap Amazon bluetooth MMCX adapter broke, I bought the not-too-cheap DR-30 that I use most of the time now, and I am impressed: Because it is not true wireless, I can tuck the cable under my clothes, shielding most of the noise and wind, even while biking through stormy Berlin or in a noisy car. The main noise people tend to complain about is rustling plastic or tap water.
All the while I also happened upon a set of the JBL E65BTNC, noise-cancelling bluetooth over-ear headphones that served as a welcome addition for longer listening on the go, sometimes even when running. Unfortunately they fell into the sea once and broke, so I have been considering getting another used pair or a more repairable variant like the Fairbuds XL or Shiftsound BNO. But for now, my other pairs supply me just fine. Just missing a pair of cable In-Ears for In-Ear-Monitoring on stage.
EDIT March 2024:
Recently I ended up purchasing the Fairbuds XL after comparisons saying they are comparable to Shiftsound but at better repairability. Just two little complaints:
- active noise cancelling is triggered by wind, meaning I usually turn it off on a run
- switching between ANC modes is slow because you have to cycle through the three modes and always wait for the announcement of the next mode to finish
Sound and handling are otherwise very good.