Nearly a year ago (I can't believe it's been that long) I made a post on glasses and whether you should wear glasses for your headshot session. My basic answer was "if you wear them all the time, then wear them in your headshot, because your headshot needs to look like how you most often look." My answer still stands. (And I'd like to add that if you wear your dentures often, then you should have teeth in your headshot too.)
But what about people who sometimes wear their glasses, and sometimes do not? Aha! What are they to do? Glasses or no glasses??
If you're looking for some kind of overarching Biblical commandment on how headshots should or should not have glasses in them, you won't find that here. Because it doesn't exist. It's entirely up to you! If you wear glasses sometimes, most times, or even hardly ever but want the option in your photo, then work with a photographer who is willing to let you take some photos with your glasses and some without. Then you can have one of each and choose the look you want to portray for whatever it is you are using the headshot for. So you can say, "I think I'll send the headshot of me with glasses with the press release to Forbes Magazine," or, "I think I'll send the headshot of me without glasses to my 90210 audition."
I also heard someone ask me once if they need to take their lenses out of their glasses for the photo session, so the glasses don't pick up any light reflections. Good gravy, no! A good photographer knows how to light for glasses so there are no reflections of any kind. (see the photo in this post- no reflections! I get a cookie for a job well done as photographer...) In your photo session, ask to see a few of the first photos the photographer took when you were wearing glasses, and if you see reflections... yell at the photographer.
Tell him or her that they need to fix it so there are no reflections. If they say they cannot... fire them. They failed.
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