Cloudy days is considered to be ideal for photography for several different reasons. First, it is easy to shoot photos, you won’t be squinting through your entire photo session which is great for the eyes. Second, the clouds create a giant softbox above your head that softens the light. Soft light is important because it is universally flattering. You won’t have any harsh shadows on your face so the pictures won’t have any drastic area of contrast that make you go, “wow, is my nose really that big?” You’re skin will look smooth and silky and any imperfections with your skin won’t be distracting. Shooting on a cloudy day is safe because you can be posed in any direction, which opens up more possibilities that direct sunshine. It is a safe shooting environment as long as it isn’t windy or cold. The downfall to cloudy days is they might lack the drama that bright sun provides. No sunflares, no backlighting, and no sunset.
Sometimes, I actually prefer to shoot in bright sun because it makes for more dramatic photos. You can see in the examples below that by positioning my subjects with their back to the sun, I can make them pop from the background because of the “rim lighting” around their hair and shoulders. When the sun pokes through trees in the background you get that beautiful background and that has a little variety in it. As long as my subjects aren’t facing the sun, and their faces are in shadow, we’ll end up with pleasing results.
Shooting in the wind, whether it is sunny or cloudy is usually problematic. Unlike me, most of my subjects have hair that and it just won’t stay put! You can’t hide from the wind as easily as you can hide from the sun. A small breeze can be useful in a couple different ways. A breeze adds motion to your shoot by letting your dress or veil blow around and keeps you cool during those hot summer months. It also keeps the pesky bugs away.