Shooting portraits outdoors on sunny days has often been a recipe for disappointment.  If you have the subject face the sun, you’ll usually get good illumination of the face, but the eyes will squint because of the brightness of the sun.  If you have the subject face away from the sun, you can solve the squinting eyes, but the backlit face will often be much darker than the background (a silhouetting effect caused by automatic-exposure cameras which try to make the average of the scene a middle gray), and you can get flare as the sun may well be shining onto the glass elements of the lens.

 

My solution has been to use a flash in conjunction with a lens shade.  I will try shoot in the morning and put the sun behind or to the side of the subject; the subject is much less likely to squint if the sun isn’t in their eyes.  I will use the lens shade to prevent the flare that otherwise comes from having the sun shine on the lens.  Using the flash will illuminate the shadows on the face, thus reducing the extreme contrast that at times approaches a silhouette of the subject.

 

Using fill-flash needs only a little thought.  First, recognize that the power of the flash is strongest at close range; when you’re far from your subject, it is difficult (expensive and cumbersome) to marshall enough flash power to approach the illumination of the sun.  Therefore, keep your flash (camera) within a few feet of your subject.  Second, pay attention to the ratio of illumination between the sun and the flash.  Typically, you’ll use the ambient (sun) light as the determiner of your aperture and shutter speed; then you’ll add flash to this exposure to add light to the shadows.