Creating lit portraits during the day isn't easy because of limitations on aperture, sync speed and flash power. However, it's an interesting look that can't always be accomplished with natural light and a reflector alone. I always feel that it looks very editorial. Adding this skill to your bag of tricks will not only make your location portraits look better, but may also improve your speed and capabilities in the studio.
I'm going to look at the balancing act between all the variables that daytime shoots bring, and how to be able to quickly and easily set up a lit portrait while accounting for these. Then I'm going to go through some basic daytime setups to get you up and running. Ryan Alexander came out to be my guinea pig for the demo shoot in the hopes of getting some new urban editorial shots, so special thanks to him.
1. Begin With the Background
When balancing your lighting layers, you have to start somewhere. Let's start with our background, which I find easiest. I'm going to set the camera to 200 ISO for lowest noise, the shutter speed just below sync limit on my camera at 1/160th, and then I set the aperture at f/5.6 because that's where my lens is the sharpest. These are the only reasons, it just gives us somewhere to start. Let's look at the first test shot.

The subject is ok, but the background and sky need to be brought down a fair way. As it is, the ambience of the image is lost. There's no point in artificially lighting a subject if you're going to then lose highlight detail in other areas. Also, the higher exposure of the background is putting a lot of similiarly-exposed detail around the subject which is distracting.
Let's dial it back until it's properly exposed. Since I'm already on minimum ISO, and can't increase my shutter speed or I'll lose flash sync, I have to decrease the aperture. If I increase the f/stop to say, f/11, I'm now about a stop or so underexposed on the background, the sky is properly exposed, and we have a nice cinematic background to use.

2. Balancing the Foreground
Dropping the aperture, of course, also drops the flash exposure. The only way to make up for this is by dialing up the flash power on the unit, since all of the camera settings are now locked in for the background. So instead of 1/16th power, where I'd normally start the lighting test, I'm going to start at 1/2.

From here I can massage the settings back and forth. If I'm happy with the exposure, the only thing I really need to worry about is the the depth of field. Just keep in mind that instead of the traditional exposure "triangle," you're now dealing with a "square." You have four things to balance.
3. Reducing the Depth of Field
What happens, though, when you decide to reduce the depth of field? You flick open your aperture, and get greeted by a mostly white screen.

You can't reduce your low or minimum ISO to compensate, and you're already shooting at your maximum sync speed. So what do you do?
Enter the variable neutral density filter (VND filter). Now you can adjust your exposure level without changing any camera or flash settings, all while maintaining a wide-open aperture.
Popping this on the lens and dropping it down to about -3EV gives us the same exposure as before, but with a shallow depth of field!

However, because you're killing all exposure with this, not just the ambient. You'll have to dial the flash up the same amount you increased the VND filter power. If you're already working at near full power on your speedlight, you may have to add a second into the mix. This isn't necessarily a bad thing, since it'll save battery life and reduce recycle time.
4. Getting Started
Let's take a look at some basic setups utilising the techniques I've described, and put them together in different ways.
First, I'm going to do the most basic of run and gun daytime techniques, which can work well depending on how low or diffused the sun is. For this one, we'll use the sun as the key light and use the flash for a fill light.
If the sun's very low, it's a nice light, but it will also be a very orange colored light. You may want to use an orange gel on your flash to match. If the sun's high, there may be some hard shadows that you won't be able to completely eliminate. This isn't necessarily a bad thing in all situations, though.
Here's the version I did. Though the sun was out, it was lightly diffused through some thin clouds and tree branches.

Ryan's clearly more a part of his surroundings, since the sun is lighting everything the same, but the combined depth of field and reduction of shadows due to the flash fill makes him stand out strongly regardless.
5. More Flash
It can look a little harsh when the sun is more direct, especially with female subjects. Here's a different shoot, all natural light, with Ryan where the sun was unfiltered and the shadows are crisp.

While a hard nose shadow would be lessened with flash fill, if you don't want that strong line across the face, it would be better to turn your subject out of the sun, use it as backlighting, and then light their face with flash. This gives you complete control over the shadows on the face, and allows you to stylise the image with sunlight.

Here I'm using the sun to flare through the top of the image and dapple the concrete for an interesting background, whilst lighting Ryan up entirely with flash. The sun also provides some rim around the head and neck for separation against the darker background.
6. Filling With The Sun
If you really want your subject to pop, you can use the ambient sunlight as a fill and blast your subject with a flash for a key light. This technique is tricky though, as it's purely style. There's little subtlety involved when the subject is brighter than the sun and can easily look bad without some care.
Generally here you don't want to turn your ambient down more than around a stop, maybe -1.3EV at the most. Then expose your subject correctly. Keeping the foreground and background relatively close together stops it looking overly fake, but allows plenty of leeway in post for as much or as little styling as you want.

Clearly we lose the subtlety of the earlier shots, and have instead an off-camera flash portrait. Nothing intrinsically wrong with this style for a variety of purposes, unless you're one of those photographers who shoots swimwear at sunset on the beach with it.
7. Zoom or Grid
When you zoom the flash in all the way through a shoot-through umbrella, it can produce a grid-like effect. I wanted to use this for an urban shot with a street-portrait kind of feel. It would usually be better with a bare speedlight through a grid, but since that was the one thing I'd forgotten to bring, I had to make do.
The initial location I had in mind had been fenced off for some reason, so after a little driving around we found this nice fire escape with the dropping sun falling softly on it through thin but increasing clouds.
I set the speedlight at its longest zoom setting of 105mm, and softened up the edges to be grid-like with the shoot-through umbrella, whilst placing the whole thing as close to Ryan as I could. This really limited the size of the pool of light it was throwing out.

8. Wrapping Up
There's clearly a significant difference in the aesthetic and percieved quality of these daytime speedlight portraits when compared to your average full-sun snap. I didn't find any major difficulties with any of the techniques. They only took around 3-4 minutes to set up, and that was mainly just due to weighing down the light stand. A convenient sandbag would slash the time to a couple of minutes. Just remember to take spare batteries. The flash was on 1/8th to full power the whole time to counteract the daylight, so I really burnt through the batteries.

It seems to me that the main advantage of these techniques, all accomplished with a single YN-560II through a white umbrella just off-camera, is that we're less enslaved to the weather and time of day for good light.
Whether it's street portraiture or an engagement session, understanding how off-camera lighting can work to your advantage during traditionally "unusable" times of day is another arrow in your quiver.
Questions? Comments? Hit up the comments below!
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