When you get called in to audition the casting director would like you to look like your headshot that you submitted. So, your headshots need to be kept current. Depending on how much you change will depend on how often you need to get new headshots.
Hair is the primary factor. If you cut it, color it or do anything drastic you will need to re-shoot. Weight is also a factor. If you lost or gained more than 10 lbs, you usually need to get new headshots. Then of course time itself will date a headshot. What you are wearing and whatever trends may be happening as far as headshots in general will demand you to get new headshots.
You can get a new headshot made and suddenly start going out on tons of auditions and get a lot of good work. But after a while all the casting directors have seen your headshot dozens of times and it no longer has the same impact. Instinctively casting directors respond better to fresh headshots. This does not mean that you need to re-shoot entirely. You can simply take another image from the original shoot and use that. If you have planned out your photo shoot and used a good photographer you will have plenty of shots to choose from and you can rotate them to keep your promo fresh.
Headshot trends do shift, but slowly. Headshots in the 80s were super tight in on the face. Top of the shoulders to top of the hair and of course at that time they were all black and white. In the 90s there was a huge trend on three quarter shots, which are from about the knees up. Then when color became cheaper in the late 90s and early 00s then people were wearing bright colors to grab the casting directors attention.
Studio shots suddenly had lots of draping fabrics with lots of color. Then in 02 we had smooth back grounds with soft greens and cool blues with the actor now fully out of the three quarter trend into waist up or tight in. A lot of actors in the last two years have been printing their headshots horizontally which ads a more film like touch to the shot. I know a few casting directors who hate this because flipping through is not as steady flowed. But, I also know a few casting directors who love it because it's easier for them to sell the talent to producers and directors who instinctively like that feel to the headshot. It is really up to you and your agent and manager.
Fashion trends do shift and can date your images. If you are looking to take shots and have them be useful for more than a year then you need to take clothing into account. Keep things simple and classic without being boring.
Typically, you should get fresh shots every year. If you are under 16 then you should get them every six months. The actors and actresses who do their shots annually are continually inspiring themselves by creating on what they are doing. Their shots get better and better because they are more and more comfortable with who they are and what they are doing. Casting directors notice new shots and look at it as progress being made on that persons career. It's fun and it refocuses you on what you are doing. Statistically my clients who shoot annually do better.
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