What should I, shouldn't I, why?!
I get asked by everyone one of my clients, a large number of inquiries and almost all potential clients the one question. What do I wear for my headshot session. My biggest concern is that someone is wearing something they are comfortable in. It is already uncomfortable enough just being in front of the camera, I don't want the person I am shooting to compound this by wearing something they wouldn't normally wear.
For headshots, keep it simple!
I can't stress this enough, a headshot is supposed to be all about you. Your personality will come through and what you are wearing shouldn't distract from the goal of this shot, highlighting you. Staying away from crazy / busy patterns, colors that wash you out and complicated layers are good places to start. For actors I typically want to see 8-12 different looks. These are headshots so we are really seeing just below the shoulders and up, just the tops matter. Different colors, different collars, some collars, some crew, some V-neck, a number of different looks that you would normally wear!
Corporate / professional clients the same as above. You may want shots in a suit, if so bring a couple different jacket, tie, shirt options. Bring some casual pieces with different looks. I always want my clients to walk out with a number of different shots in different looks. You may want a really professional looking shot on LinkedIn where you may want something more casual to post on your facebook, or Google+ or somewhere else.
Nothing to big, too flashy, if you are wearing earrings, I really encourage you to use just studs that you like, nothing hanging down, a necklace, let's keep it simple. Be prepared to do shots without it as well.
Other than that, relax, let your self come through in your images.