How often should you get a new headshot really depends on a few factors and when your last professional headshot was taken.   I usually recommend my clients to update their headshots every 1.5 to 2 years.  Over the course of two years, you may have changed careers or roles, or your personal appearance may have also changed so you do want to portray a current photo of yourself for whatever activity or role you may need it for. 

Usually, you should get a new headshot as often as the following is true:

• You no longer look like your current headshots.
• You do not like your current headshots.
• You changed your hair color.
• You have a different hair cut or style it differently (curly vs. flattened).
• You have grown facial hair -- applicable to men.
• You have a significant gain or loss of weight.
• You have undergone cosmetic changes to your face or body.
• You have a different role or changed careers.