I have many different headphones and earbuds, I found that usually in headphones cheap purchase = too expensive purchase.
Of course high-end = high-end but those prices aren't available for most people, including me
but there's some really nice mid-range stuff available.
these two are my favorites
For listening to music and gaming, Beyer Dynamic DT-990 PRO (open)
They're a little colored in the low-end of the spectrum which makes it real nice and warm sounding headphones.
For studio/reference I'd recommend the DT 880 which has a flatter response but lack the warmth.
I like these when listening for pleasure. Music sounds clear, defined, and warm.
Big chance you'll hear stuff you have never heard before in the music you've been playing for years already when using these after always having used cheap headphones.
They have big replaceable over-ear cushions of very light and soft material. The fabric is velvet-ish and feels real comfortable. The weight of the headphones lies on the top of my head.
No pressure on my ear shells at all, they fit right in there and the open construction doesn't make my ears too hot either.
I could wear them all day.
For outdoor or in bed I mainly use the sennheiser CX 300-II precision.
They're very small, sound very nice and can be found for under 50 euro. Because theyre so small I can even lay on my cushion with one ear to watch something on my phone.
The build quality is very good too. I've been using these almost daily, for over 4 years already.
I also have some great sounding Sure in-ears but they're big and uncomfortable. Better for in-ear monitoring on stage.
I also have some Sony's that sound good but they're mainly nice outdoor, not in bed for instance because they stick out.
And a lot of cheaper ones that just sound bad.
These sennheisers are the ones I use most because of the sum of their size, comfort and sound quality.
The wire does have a nasty tangle tendency though, there's no microphone or music control but hey, can't have it all for under 50
An exception to the cheap purchase = too expensive purchase was, to my big pleasant surprise; this:
The Edifier R1280T
At 89€ I would have never suspected them to sound this good.
Nice clear sound in the mids and high, and a good solid bass.
The high is very directional though so speaker placement is preferred at ear height and a little further away, but man... the sound/build quality vs price ratio... I would have never suspected this...
They sound better than the Teufel speakers I have in my living room.
I'd really recommend these over any other bookshelf or desktop speaker in the same price range and even over a lot more expensive ones too.