Should I get my hair and makeup done for a headshot?
I am going to say definitely maybe.
HEADSHOTS WITH A PURPOSE
My purpose for your headshot is to show its viewers an accurate and flattering image of you. If they saw your headshot then met you at an interview or audition or saw you presenting onstage or passed you on the street they’d recognize you because of that headshot. If they do not recognize you, then your headshot has not fulfilled its purpose.
YOU ALREADY HAVE A GOOD FOUNDATION
Decisions about your headshot are then guided with that purpose in mind. For makeup, I strongly recommend using restraint with foundation. Our skin has texture and when that texture is covered up or muted, whether from heavy foundation or digitally blurring it, then it will look unnatural. A headshot will be a tighter cropped photo that skin texture might be visible, depending on how it is viewed. Skin without texture will make the viewer question, maybe subconsciously, the photo's reality or accuracy. It will look off. We humans are very perceptive and we expect certain things to be present and look a certain way when we are looking at the world or looking at representations of the world. We intuitively know what blue a sky should be and we intuitively know what a human face should look like.
KINDER AND GENTLER HEADSHOTS
But take comfort, the way I light and shoot and retouch headshots is intentionally kind to skin texture. I don't aim to eliminate texture and depth in my headshots, but I do aim to keep it all looking its best. So you do not need to worry about getting your makeup artist to make you look like a mannequin with perfectly smooth but unnatural skin. Tell them to keep it natural—pretty please.
BE YOU
I’ll go back to my original goal for a headshot—it should look like you! If you decide to get your hair and makeup done, have it done in a way that is natural and is consistent with your day-to-day style. Remember, people need to easily recognize you when they first meet you in person.
Look your best, which means looking like you.