You don't have to reinvent the wheel every time you need to do a portrait outdoors. Groups can be tough enough, and lighting an outdoor group, large or small, doesn't have to be.
If you are super skilled you can add extra kicks and background lighting elements, but get the basic group lit with beautifully balanced, studio-quality light FIRST! This is how we have done it, and continue to do it for consistent results that DON'T NEED TO BE FIXED later.
We usually use a pair of GODOX AD Pro300 lights in approx 3x4 softboxes, which are, (of late), inexpensive GODOX modifiers. When you use boxes or umbrellas, you'll need help holding onto them. If you use smaller set-ups, without modifiers or bare bulb sources, those are less likely to be knocked over by a little wind. Though the quality of light differs with the size and proximity of your light source, either way, the goal is to get THE SAME lighting value and directional pattern on everyone. Nice subject separation from the background, and utilizing the available light well are our recommended starting points. Get those lights as close as you can and high enough to have a downward pitch for best results.
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