If you choose an outdoor portrait location, there's always a chance that the weather will spoil the party. Sometimes you'll just have to take a chance and hope it stays dry, but try to have a backup in case the weather turns bad.
Look for a location which has some sort of shelter nearby, such as a bridge, bandstand, or cafe. These can be life-savers during a quick shower, helping you keep yourself, your equipment, and your subject dry - particularly important if they're paying!
If the weather gets really bad you may even be able to move your whole photoshoot under cover. With open-sided shelter you can often recompose to keep a natural background behind your subject, and as long as the lighting is good enough nobody will ever tell you weren't fully outdoors.
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