I have headphones ranging from under $100 to pushing $1000... and there's a difference.
The trick is this - the $1000 headphones are pretty much flat across the spectrum. If you're mixing a band or a track, that's what you might want, clarity and accuracy. I have them for that specific purpose and use them rarely, for that purpose.
Why? They don't really sound "good," they sound "accurate," and usually accurate comes across as somewhat harsh. Certainly not something you want to listen to on a regular basis.
One of the best things I ever did for my in-ear monitors that I use when performing is to learn about the Harman ideal response curve (
https://jazztimes.com/reviews/products-and-gear/audio-files-the-harman-curve/ is a place to learn a bit) and EQ my in-ear mix accordingly.
Few headphones are flat on a frequency graph, and even fewer come across that way in real life. There is a (long tedious) process (involving sweeps of frequencies and various sine waves at various frequencies) that you can use to determine where the peaks and valleys are in your headphones. I've done it, it's not for the faint of heart, it took me about 2 1/2 hours with my in-ears (Shure 535) and I came back the next day to check my work after my ears had rested.
Once you "flatten" your headphones, it's dead simple to apply that ideal response curve and WOW what a difference in terms of "enjoyability."
I can now listen on headphones for a lot longer without feeling fatigued, and I actually enjoy what I am hearing.
If you are using a DAW, and have the ability to EQ your headphone mix, you can do it on nearly any set of headphones with a little patience. If you are just plugging straight in to something, notice the response of newer headphones and see that many are migrating towards that idea response curve. The closer you get, the happier you may be.