[Amish]

Guess it depends on each person's idea of what is not cheap. For me the first set of good cans I bought were Sony V6 but after that the Sony XB700 then Grado 325. I've owned a handful of non-cheap cans since but still own many of them.

 

[Tasty Mushroom]

My first non cheap cans were the Sennheiser 555s which stayed with me until they stopped working. From here I went after the HD600.

 

[Pirakaphile]

The grado SR80i, which I demoed for 2 hours in the audio store on my phone. Great introduction to open-ear cans, and since then I've been hesitant to get closed cans for portable use. Loved them to bits, and they're still very good for the price, but they're out of the game in comparison to what I've got now.

 

[PalJoey]

My first proper (as opposed to the cheapest available) headphones, the black'n'red Sennheiser HD450s. Used them and loved them for years and years.
 

 

[linglingjr]

Mine were AKG K272s:

 
I really wanted to get K701s because they "looked cool" and were only $200 ish.  And then I started looking into how much power they need to sound good and that got me into head fi and eventually justified me spending $450 on a headphone amp and even more on headphones.  

 

[cskippy]

First non cheapo pair of headphones where Beyerdynamic DT 880 pro.  They are very underrated.  However, I can see why people complain about the tizzy treble.  A good dac and amp are a must to get the most out of them.

 

[kramer5150]

in 1984 I was 13.  I bought a pair of sennheisr MS100 for around $75-80.  That was a LOT of dough back then.
 

 

 
On my wrist was a casio DW-5200

 
 
I wish I still had them both

 

[funkymartyn]

  My first proper (as opposed to the cheapest available) headphones, the black'n'red Sennheiser HD450s. Used them and loved them for years and years.
 

These were also my start to real named headphones....from argos if I remember correctly...in sale....Then picked up a pair of GRADO sr60, from ebay, ..thern the Grado sr 325i also ebay....its never ending...and last of all my sennheiser HD 580 superfi sale brand new £80.......and all my phones still it top mint condition....

 

[funkymartyn]

Still got a load more headphones..like two Bluetooth, two wireless, and loads of others, inc, Goldring DR100.....etc

 

[bar1]

My first headphone, Beyerdynamic DT 440. Early 80's. My set died late 90's.
 

 

 

[Mr Rick]

My first cans looked a lot like these.
 

 
But, I spent years working with these on my melon
 
 

 
.

 

[akfortyseven]

UE6000 although I did get them fairly cheap

 

[Audiophile2]

Klipsch s5i sounded great but went through 3 pairs before switching to Bose ie80s (don't sound great, but better than average and don't break as easily.) The home listening, bought a pair of grados sr225i

 

[Lehcs]

 

[Shaffer]

Does the original SR80 count? If so, that's what I had. If not, we'll have to flash forward ~20 years to DT990pro.