I’ve gone pretty far down the headphone rabbit hole in the past 6 years. Currently I have 7 headphone amps, 3 of which can serve as system preamp for my desktop audio system (2 x 2-way nearfield monitors + sub); and 5 or 6 headphones at any given time.
My favorite headphones are the heirloom-quality wooden earcup designs of ZMF headphones. I have 3 of those models currently; had and sold 2 others. I can firmly recommend the Verite Open, the best dynamic driver headphone I’ve ever heard (and I’ve heard many).
Headphones with planar/orthostatic drivers are a whole other bag. I really love certain sonic qualities that planars excel at. I currently have 2 planars: 1 is the legacy ZMF design, the Ori (lovely sounding closed back design); and tied w/the Verite Open for best headphone here is the Final D8000. Both of these headphones manage to combine a lot of resolution & speed with an organic, musical sound that is the opposite of the forensic/accurate thing found in some pricey headphones (and speaker, of course).
Speakers systems & headphones are both audio reproduction, but they are relatively dissimilar. I’ve come to love the intimacy and drama of really good headphones. Of course, no headphone can light up a room like a speaker system (horses for courses).