And, as usual, my answer is, “it depends.”
The first question to ask is, “do you always wear your glasses?” If the answer is yes, then put your darn glasses on for the headshot. A headshot is supposed to be a photograph of you, depicting what you generally look like on a regular basis… while looking your best and in a good mood, of course. So if you’re always wearing your glasses, then wear them in your headshot.
Now you might be thinking, “I always wear my glasses, but sometimes I take them off when I’m on stage… or I want people I’m auditioning for to know that I can go without glasses too…” Aha! Very good point. Gold star. Most people look completely different with and without their glasses, so if you want people looking at your headshot to see both of their options, what do you do? If you’re expecting an answer like “you should always wear your glasses in a headshot” or “you should never wear your glasses in a headshot” then I apologize, but you’re not going to get that here.
There is no right or wrong answer to something like that- it all depends on what you want, need, and are comfortable with. Here’s a case study with Victoria DeFrancesco Soto. She came to me asking for headshots for publicity purposes as a television personality and expert on minority figures in international politics. (With the recent Obama campaign, she’s obviously been a busy lady…) She normally doesn’t wear her glasses on camera, but is looking to expand her reach and believes some people might think she looks more learned and professional with her glasses on. So we snapped most of her photos without glasses, but made sure to grab a handful with her glasses on.
Now she has the option between two different looks and can use the glasses headshot for gigs she knows she’ll wear her glasses for, and the other one for purposes that she doesn’t think having glasses on will necessarily give her a leg up.
Like with any question about determining your look for a headshot, just remember to go with your gut and what you believe depicts you at your best. And ask yourself simple questions like, “do I ever wear my glasses?” And if your answer is, “only when I wake up in the morning to get myself from the bedroom to the bathroom where my contacts live, I’ll never wear them outside!” then of course you should leave the glasses off for the headshot. Or maybe ask yourself the question, “am I a Groucho Marx impersonator?” If the answer is yes, put your Groucho glasses on.
And find a headshot photographer who will ask you these questions so he or she can help you set up the best possible photo.