I'm not new to headphones,used them as a musician for years, but not for serious listening.
Mostly because I never had any really good phones and because I ner had a really good headphone output in any of my systems ,except the Cary 300sei.
That was my undoing, and had I tried a few good headphone with it, I would have never let it go and use it just as a headphone unit.
What I can say is that your impression of a pair of headphones depends on what they are pluged into, so I'd suggest when auditioning phones, try out some of the better headphone amps to really get the measure of the phones.
In fact I'd say that the better the headphone amp, the better sound you'll get from even modest phones.
Case in point I have the old Grado SR60's, and they never really impressed until I tried them in the Cary.
Now I'm burning in a pair of AKG K702 in a Yamaha receiver
The sound of the AKG is nowhere near as good as it is when I played them in my Burson HD160 even when they were fresh out of the box.
The better headphone amp lets you hear the difference between the Grado and AKG phones, the Yamaha not so much.
So if you spring for any of the better phones, make sure you factor in a decent headphone amp,if not then stick to a cheap pair of cans.
I'm just tipping my toes into the haedphone waters, but even with what I've got I'm more than impressed with what you can get for so little money.
In the future I may go into the deep end of the pool.
Upgrading the phones and then the amp.