I often get asked about the practicality of wearing glasses in headshots, with many people asking me if they should just take their glasses off for their photo. The problem is that your headshot should reflect you and how you will appear on a day to day basis, therefore if you do wear glasses regularly then they should be featured in your headshot.
Photographing a client with glasses raises several challenges – as a photographer you have to consider any reflections that may be captured in the lens of the glasses. These reflections could be anything from the lights to the camera itself. In an ideal world all my clients that do wear glasses would have an anti-reflective coating applied to the surface of the lens. This would solve all reflective problems when it comes to photographing these customers and gives the glasses a smart, clean finish. 
The chances are that you already have your glasses long before you’re having your headshot taken. In this case I would advise that you speak to your local opticians and politely request to borrow a pair of similar frames for the day or if they can pop out the lenses in your own glasses for a day.
As a photographer in this day and age it is also expected that you are something of a photoshop expert. When it comes to using photoshop, in regards to glasses in headshots, it is much more difficult than it seems. The only way around the problem of reflections is to take two different headshots of the client one with them wearing their glasses and one without. Then using photoshop you are able to create a composite image merging both those pictures together. However, this is not without it’s challenges. It is exceptionally hard to get two pictures of the client in the exact same position with the exact same expression and so often it will not work and will give an unnatural look to the finished headshot.
There are ways around this but I can’t reveal all my tricks now can I?
If you have any questions please feel free to get in touch by leaving a comment or sending me a tweet.
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Thanks for this great information because I have been wearing glasses for over 40 years and this is who I am. After retiring, I decided to try acting and take a few headshot but I was always concern about my glasses. I will get the anti reflective coating applied. Thanks again!