Unfortunately my first “good” IEM Shure e2c disintegrated in my hands on its 10th year, but my next one Ultimate Ears triple. fi 10pro is still healthy and running like a champ.
If Meze 99-Neo counts, I still use them at the office. Though, I’ve rolled their pads and done some other modifications inside the cups, too.
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Auricles. In production with various materials from 1850-1928.
Just kidding, I’m not that old, but thought I’d try to revive the topic.
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Good idea, I had never seen this topic!
I do have my first pair of headphones, the ATH-A900x I bought the first time I visited Japan. I haven’t used it in years and one day I noticed the pleather is basically disintegrating. I’m guessing it’s the humidity since I moved from a much drier climate. I do have replacement earpads I bought for $10 (can all manufacturers make their pads this cheap???) that I’ll surely throw on any day now…
The last time I heard it, it was still pretty good. Wonky tuning and extremely mediocre in the perceived technicalities, but with a little brain burn in it does get that sense of musicality right, whatever that means.
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I like this topic. I dont have my first pair of good headphones. which were a pair of dt770 80 ohm. Loved those things. I eventually had to get the dt770 proxle.
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Yes I do, and like others here it’s an HD 650 from 2007 I think?
It was made in Ireland, and I used it with a Headroom micro amp and micro DAC, great stuff I wish I’d kept!
Anyway still have the headphone which I bought for $299 from Adorama, which believe it or not was a great deal at the time! 
I cringe to think what that is in 2025 $!
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It’s not as bad as I imagined, $299 in 2007 is $465.86 in 2025. Audio equipment depreciates, but good stuff retains some residual value. I hate to consider how much I’ve spent on PCs, tablets, and phones over the years, as they’ve all gone to $0. This includes pathetically weak but gigantic 386, 486, and Pentium desktop PCs that had a fraction of the power of a $35 phone today.
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Yes, I still have my first pair of “good” headphones — they may not match today’s high-end models, but they hold a lot of sentimental value. 
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How many have yet to buy your first “good” headphones?
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My first “good pair” was a Sony MDR Z7. I still have them,