Here's my first (and current) rig:
Audio/Video Device: Dingoo A320 Multi-Console
Headphone Amp: Fiio E3
Headphones:
Sennheiser HD500 (using HD590 earcups because the original "leatherette" earcups left sticky stains around my ears)
Pretty banged up after 10 years of constant use but still sounds great when i run this with my E3 Amp. Usually used when i'm watching movies or listening to music in my room.
Sennheiser HD414 (felt kinda bored seeing the usual colours for the earpads, so i dyed them in Jungle Green

)
My first set of headphones, got this while i was still studying (now its about 13 years old) Currently my PC headphones but i do have this urge of using this outdoors
Earphones:
Sonicgear Earpump Pros with Comply Tips
Have been using this for my outdoor listening for the past year and half, the Comply plugs were a recent addition.