We're always hoping for sunshine when we intend to shoot outdoor portraits, but overcast weather can make your job so much easier and have a beautiful result! You don't have to worry about uneven lighting or harsh shadows so you can place your subjects anywhere! This also applies to sunrise and sunset times when it is bright enough but without direct sunlight. Give it a try!
Backlight your subject by putting the sun behind them and use a reflector to bounce the light back on them to create lovely lighting and catchlights!
When shooting natural light portraits find a small patch of shade. Make sure your subjects is near the edge of the shade while still fully covered by it.
Being this close to the edge will help create a direction of light and allow you to use a reflector for a nice catchlight in their eyes. This is what we refer to as 'Open Shade.'
Window light is a photographers best friend! Position your subject near a window; the window should not have any sunlight coming directly through it, but the diffused light will be very flattering for your portrait photography. You can Also use a reflector opposite the window to bounce back in some more light and slightly reduce shadows.