This part can be difficult in some cases or it can be easy. Depends how are you with seeing light, and then even when you find great interesting light you'd need to ensure it falls onto the subject(s) properly, as well have an appealing composition.
If you've just jumped into this part of the blog series I highly recommend you read the past parts as this part is spoke with the assumption you've read the past parts, as well you've learned the important part of timing which can be figured out with what gear you have and location you're shooting at. Check the index.
This post is why I shoot the way I shoot on natural light and recommend anyone in my situation, such as lack funding for assistants, don't have friends/family willing to help consistently on a bunch of natural light portrait shoots, and don't feel comfortable with any lighting equipment/modifiers in the field by themselves while you shoot. I know most others teach to have a fill, reflector, or something but this isn't doable alone (just you and a model/person), especially in a big city where tons of people pass by, or even small cities if you're paranoid like me. So the following will help you in this same situation to still create unique and amazing natural light portrait shots.
When I say easy, it can be very easy if the sky is very consistent in cloud coverage (large cloud coverage) so you have constant and consistent giant softbox type of light during your time shooting outside. Such as for example on my day shooting outdoors on Halloween 2015.
And during times its clear skies or partly cloudy you can find pockets of having great flare shots like these.
Sometimes if you're unsure and starting out shooting natural light portraits like these, simply trail and error. Such as try a shot with the subject, see how it looks, if you like it great keep doing it, if not adjust angles.
Specifically shooting the above flare shots are not easy. You will need a lens hood and a DIY lens hood to get more control... your hand! The trick to shooting against the sun is covering the sun you see in your viewfinder in order to have the AF focus, then move your hand to reveal the sun and cause that flare. Some people like it, some people don't. I personally love real and natural flares created in the field (not in post, unless I really have no choice). This can get even more trickier shooting at more open apertures like f/1.4-f/2, f/2.8 still tricky but its doable and as long as the subject isn't moving too much and you don't move too much its good, which isn't easy too, shooting wide open with 1 hand and staying on the same focal plane, so there is risk of some out of focus shots since you're shooting with just 1 hand.
Trail and Error
Shoot, shoot, and shoot some more. You will eventually see the light as you keep shooting over, over, and over without hitting the shutter on the camera and simply knowing the light will be amazing for X, Y and Z shots. That is how I found my light and how I see light.
Rule of Thumb when scheduling a natural light portrait shoot
When you're scheduling a natural light portrait shoot, generally you cannot predict 100% for sure chance of weather, such as for rain, which is obvious. So you can't shoot in a rain. But for differences in light, like planning a shoot on a cloudy day or clear skies day, you can if you really want to but be prepared to reschedule often. What I do is play it safe, schedule the shoot at my best times for golden hours and hours my camera can still perform well in ISO. I do not plan to need X type of skies to get Y type of light. If its clear skies I can still get soft light shots without a flare if necessary just gotta angle the shot without the sun which shouldn't be too hard when the sun is fairly low already.
Assuming you already have the basics down. But the compositions of what I prefer are leading lines, sometimes repetition when possible, and one of my favorites... rules of third. I'll go over this on the location scouting post. Sometimes composition lackluster, so you can either A: move to a better composition/location or B: photograph the subject close enough and with the right lens to bokeh the background much heavier to remove most of the background's composition at least.
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Keep in mind the posts in the index are in order, so if you're jumping in reading the series at 3 or 5 you should really read from 1 to above to ensure you did not miss anything.
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