I've been fascinated with "good quality" headphones since I was a kid. I remember seeing people with the neckband Sony Street Style headphones and wanted them sooooo bad (when you're a kid, 25$ is very luxurious hehe). I didn't know the concept of "sound quality" back then.
Eventually I got 'em. Then they broke. Got more cheap headphones in between... eventually started realizing I was not satisfied with the sound quality. I was finally SQ conscious... it's like I leveled up overnight
. So I bought the Sony MDR-V300, which satisfied me at the time. I was still not very informed about headphones at the time, though.
Then they broke too. No more Sony for me! I eventually got informed on headphones and bought Sennheiser PX200s. That's when I'd say my journey began. After rocking them with my portable player for about a year, I paid a visit, for the first time, to the local HiFi shop. I was there to buy (cheap) interconnects, and tried the AKG K 414 P they had on display just out of curiosity.
That's when it all really took off. The sound quality was so detailed and immersive compared to the PX200, it almost sounded too good to be true. And they weren't even really expensive! I bought them on the spot. I actually still swear by them today with my portable gear.
Later last year was when I started working on the high-quality, don't-leave-the-house headphones. I bought AKG 141 Studio with Christmas money (full retail price) and AKG K 530 with birthday money which was 15 days later (found them for half of retail price, thinking I was getting a super sweet deal).
Of course, now that I'm on Head-Fi, I realize that I'm never buying retail again. MUCH better deals to be had online and in a community where people take great care of their headphones it's like getting them new, condition wise, with the benefit of an already 'broken in' sound! Also, reading on Head-Fi really keeps me in check before I buy a pair of headphones.
Next stop for me is the K 701 + Corda Headfive. Should be a good step up from K 530 + Harman/Kardon AVR 146!