When taking photographs natural light is best--even if you're shooting indoors it is better to be by a window than to rely on overhead lights. Even if natural light is best what about the difference between bright days or cloudy days, sun in the middle of the day or at sunset? In the end choosing what type of light to shoot in has to do with preference and convenience; each type will have its pros and cons and since you don't control the weather you have to figure out ways to work with what you're given.
Bright midday light: This happens to be my least favorite type of light to shoot in, but it's sometimes what you are stuck with. It's not the exact middle of the day (when the sun is directly above) but either late morning or early afternoon when it is very bright and the sun is high in the sky. These pictures were taken around 2PM, facing the sun (left) and the sun at my back (right).
Pros: Backlit pictures (right pic) put the subject in focus and further wash out the background. The light is dynamic and interesting.
Cons: If you are facing the sun it creates harsh shadows on the face and makes the subject squint. If you choose backlit pictures you have less control of your angles; in the pictures above I like the row of houses behind me in the left picture but I can't get backlit from that angle because the position of the sun. Backlit self-portraits are really difficult to get the settings right with.
*Other options on bright days--seek out shaded areas like the woods or the shadows between buildings to shoot in.

The Golden Hour: This is a little before or a little after sunset/sunrise; it is most people's favorite time to take pictures (of course you have to have a flexible schedule to choose to work at this time). These pictures were taken a few minutes after the sun set behind the buildings in my area (technically the sun was still above the horizon line); in the picture on the left I faced the set sun and on the right the sun was behind my back.
Pros: The light is soft and colors are rich. The subject can look directly towards the source of the light without squinting and there are less shadows in pictures.
Cons: You have a narrow window of time and will have to adjust your settings as the light fades. If the sun is setting it will eventually get too dark for pictures and if the sun is rising you'll go from soft light to bright light. Once again you have to pay attention to the direction of the light (in this case you typically want the subject to face the sun rather than have it at their back, although backlit at sunset can work sometimes).

Cloudy Days: My favorite type of light for pictures is actually a cloudy day.
Pros: No harsh shadows on the face and the light is consistent, you don't have to adjust your settings often. Subject can face any direction more easily and you can maintain more colors in the background than on a bright day. No time constraints--as long as the sky is cloudy you can continue working. Also, less people outside!
Cons: Less dramatic images because the light isn't spectacular and the light can be flat and unflattering.
Other things to note: All of today's pictures are completely unedited to illustrate the differences in light, there is obviously editing work you can do after you take pictures to help alleviate the cons. When you're working with different sorts of light you once again have to adjust your settings. On very bright days even with a low ISO and shutter speed, you will also have to adjust your f-stop to a higher aperture meaning your background can't be as blurred. When you shoot in softer light (sunset or a cloudy day) you can typically keep your f-stop lower and maintain a more blurred background. If you're confused by what I mean by f-stops and so on, I explain them more thoroughly in previous photo tip posts.
**I'm wearing: Bonlook glasses, Pepa Loves dress, thrifted belt, and Seychelles flats.**

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