Actors always ask what kind of photos they should upload onto the casting sites or what kind of "looks" they should take at their next photoshoot. While it's good to have a variety, it isn't necessary to have 25 "looks" or wear major costumes.
First of all, you need a BASIC, main headshot. Casual and versatile. If you are on a budget and can only print up one photo, this is the one you would use. A SMILE would be great here.
You also need a BUSINESS shot. Something you could wear to the office, a courtroom, a wedding, a nice restaurant. This could be your non-smiley shot.
And if you have room in your budget for additional photos, you can add character looks. Choose a cute/nerdy/quirky or badass/thug or drunk/junkie/homeless or rockstar/biker dude look. This could also be your body shot for print work: If you have tats, this would be good place to showcase them. If you have a rockin' bathing suit body or great hands, feet and/or legs, SHOW THEM OFF HERE!
Badass biker dude
Make sure you don't have the same pose, smile, expression in each shot. A former client posted 5 or 6 photos online but his facial expression never changed in any shot. It looked like he had photoshopped his face onto different bodies. Just sayin'.
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