Tips on photographing someone who is wearing glasses?
I have found it helpful to have the subject tip their head down just a bit, just enough to pull the chin in & lose the glare off the glasses & the light to bounce off the rim..it's very slight tip & for the most part goes un noticed in the final image.
use a diffuser on your flash if possible
use reflected lighting or natural lighting if possible.
Matthews suggestion works well for glasses with larger lenses, but smaller lenses look like they are falling off the subject....That is when I have the subject tilt their head.
There are probably more but these are what I use most.
Here are some examples of having the subject just tilt their heads a bit
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