Most people are not like my dad, who has had the same haircut since the late 1950’s*. We like to change our look here and there and even on a daily basis… one day we’ve got a beard, the next day it’s a mustache. The day after that it has vanished to mustache heaven.
Although I wear contacts 95% of the time, I walk my dog every morning before I put my contacts in, and I always see the same early morning commuters and dog walkers around the neighborhood who only see me in my big, black librarian glasses and red and white knitted hat. They must think I always dress like I’m in a “Where’s Waldo” book.
So how should your headshot look if you’ve got so many different looks? I always vote for the majority. (we’re not talking about political stances, by the way, just portraiture trends.) If you usually wear your glasses when meeting your clients for the first time, then wear your glasses in your headshot. If you’re usually clean shaven and only sport a mustache to go with your Tom Selleck Halloween costume, then leave the mustache at home for your headshot.
Or in some cases- if you’re an actor and want to have multiple looks for different types of auditions, then take photos with all those looks so you’ll have a big pool to choose from. Auditioning for a lumberjack role? Send them that bearded headshot! Trying for the part of a young librarian? Send them the naked cheeks and spectacles look!