I probably don't have the best ears, because I find that my ears tend to be pretty forgiving of a guitar tone all by itself. They adjust to the relative brightness of a tone and it sounds okay. For example, my studio monitors are brighter than my headphones. If I change from one to the other the tone immediately sounds too bright/dark depending on the direction of the change. But after a short while it sounds "normal."
BUT, if I listen to my guitar tone AGAINST music, then I can hear immediately, and indefinitely, if it sounds too bright, too dull, has hiss, or whatever. I've learned this as a part time sound tech, too. Never EQ an instrument, beyond a quick rough-in, by itself. It's a waste of time. At least for me with my talent level. I'm sure those with "golden ears" can much better judge tones stand-alone.
Additionally, directly to the OP issue, I find that it is easy to miss certain problem areas with a tone on a given listening system. For ex, I would tend to dial in too much fizz using just my headphones (which are less bright than my monitors) because I just can't hear it as well.