There's no hard and fast rule for how often you should take new headshots. Some people change faster than others, while some don't change much at all. Here are a few things to help you decide if it’s time for new pictures.
You no longer look like your current headshots
Your current pictures aren't getting you out on auditions as often as they first did
Your current headshots are limiting in nature and perhaps only suited for commercial or theatrical
If you have the luxury of keeping your portfolio fresh with new images a couple of times a year, then do it. But if the headshots you have now are working for you there's no need to spend the money until they don't.
MY ADVICE IS TO REFRESH YOUR HEADSHOTS AROUND EVERY YEAR
Always think about the Casting Directors that didn’t bring you in. Was it the headshot? Or was it something else? The Casting Directors who’ve embraced you will likely remain fans, even when you get a new set of headshots. New headshots give you a chance to reach the CDs who weren’t persuaded to bring you in.
Remember… a new you means new headshots.