It is perfectly fine to encounter overcast weather in a photo session, and in fact, this is the perfect condition for portraits. I photographed this beautiful family in a cloudy day in Walnut Creek because I love the autumn foliage. It is hard to find a red leaves foliage in the Bay Area because we are located in the East coast. If I were in Toronto or Boston, red leaves foliage should be everywhere. Walnut Creek is a nice location if you want some autumn feeling in the photos.
My style is to find good location in seemingly ordinary settings where you can have soft natural light, and a contrasting background. This awesome family just smiled naturally in front of the camera, got a lot of great shots!