I can tell the difference between $30 headphones and $300 headphones, you could probably tell too. But between $300 and $3000? I wouldn't trust myself.

I think to even try, you need to set up an A/B system and precisely match levels. If you don't match levels, the louder one will always sound better.

I've tried it before, but it's hard to match levels. It's even harder if you're swapping headphones or earbuds.