I can see how it could have been considered more negative in the past, when wearing glasses was itself a negative thing. Anyone remember the old line, “Men don’t make passes at girls who wear glasses”? Needing glasses once meant that you were sickly, elderly, etc. And they’re still used as shorthand for “nerd” in movies and TV.
But I think that now, glasses are sufficiently commonplace that there’s almost no value judgment attached. In fact, I was just in a meeting with about 10 people - young, old, fit, fat, men, women - and at some point, I noticed that everyone was wearing glasses.
The history book I used as a high school senior (1976-77) described Mahatma Gandhi as “a wiry, bespectacled man”. He may have been bald and nerdy, but he certainly wasn’t a fat douchebag principal.
My guess is the prejudice against imperfect vision comes from ancient religious tradition. I seem to recall that according to Old Mosaic Law, those whose vision was imperfect were unclean and could not enter the temple. (Those whose testicles were damaged or imperfect also were forbidden from entering the temple.)
To me, “bespectacled” means a little more than just that the person wears glasses. It connotes that the glasses stand out, somehow. That they are one of the more noteworthy features of whoever we’re describing. We think “Gandhi” we think of white cloth and glasses. Glasses on a baseball player is unusual. And so forth.
But I don’t see it a negative term. Just descriptive.
It carries connotations of pomposity and self-importance to me. Not on the part of the person being described, but on the part of the speaker/writer. Nobody actually uses that word any more, so it calls up images of old novels full of tortured, overly dense prose.
As a fat, bald, bespectacled man, I am offended by this.
…No, not really.* I’m with everyone who says there’s no baggage to the word one way or another.
*I mean I’m not really offended. I really am a fat, bald, bespectacled man, though. Working on the fat part; bald and bespectacled are here to stay.