Yes and No. There are so many preferred sounds out there that a $300 and a $3000 headphone are likely to be quite different, and you would expect the $3000 head

Yes and No. There are so many preferred sounds out there that a $300 and a $3000 headphone are likely to be quite different, and you would expect the $3000 headphone to be technically better, but it comes down to preference. I have a $1000 pair of headphones, and they do just about everything really well, but I also have cheaper headphones that are more accurate (to different target curves, but that is getting into psychoacoustics), or more enjoyable for certain genres. Price doesn't necessarily correspond to audio quality very well. For example, Ultrasone sells some objectively terrible headphones for $3000.