In the seventies, I owned Stax SR-44 electret "earspeakers", which I enjoyed a lot, but used only when I couldn't make noise. When they died in 1993, I replaced them with Grado SR60 headphones. The transition was easy, I don't recall missing the Stax.
The Grado's pretty much lived in a drawer for decades, because a bigger house allowed me to use loudspeakers most any time. I still have them and still use them occasionally, because they sound surprisingly good (better than a friend's SR80e), and they are the most comfortable headphones I've ever worn. Also, they're great for travel because I don't worry about loss or damage, and they sound better than my Sennheiser HD1 and Beyerdynamic Byron iems.
In the past couple of years however, headphone listening has become a big part of my music listening. I listen primarily while surfing the net or processing photos, which I do about four hours daily. That's about double the time I spend listening to my stereo system. I started out with low priced gear and ended up with this collection at my headphone Station:
SOtM sMs-200 Neo, Zerozone 50W linear power supply
Oyaide neo d+ Class A USB 2.0 Cable, 5V pin blocked
Schiit Eitr, Ghent Audio USB Y-cable, Topping P50 LPS & iFi iPurifier2
Audiolab 8200CD/DAC
Yorkville Studio One XLR and Cardas Neutral Reference interconnects
Hafler HA15 and Schiit & Asgard 2 headphone amps
Beyerdynamic DT 1990 Pro headphones with Analytical pads
Grado GH4 headphones
QNAP 451+ NAS
Dell Inspiron 7000 laptop via wi-fi