Gear & Technique

As with everything in photography, there are no hard and fast rules you must follow. But there are some basic guidelines which should be considered.

First and foremost is what image do you want to take? What are you wanting to convey, what feeling? How are you going to convey this? And of course, composition and everything else that is involved in Creating a Picture.

Once you've considered all of that it is time to decide on what gear to use. Obviously, this is going to be dictated by what you currently have. But I'll cover the basic considerations.

The Lens:

The lens chosen is going to dictate many factors in taking the image. It will determine what is the best aperture for sharpness, the minimum and maximum DOF you can create, and the working distance/perspective.

Focal length selection determines the working distance and perspective in an image. For portraiture a longer than "normal" focal length is generally considered "flattering" because it requires a longer working distance. This will result in the compression of some facial features. It makes noses smaller and brings eyes forward. The longer working distance also results in a greater DOF for a given aperture which allows you to get both eyes in focus. In general you're looking for something between 75-150mm.

This means a 50mm lens for a crop sensor body or an 85mm lens for a full frame body.  A zoom lens that covers that range is typical of a "kit lens" that may have come with your camera. 
Keep in mind that most zoom lenses suffer from "focus breathing." "Focus breathing" means the lens's FOV/magnification is only "accurate" at infinity focus. At all other focus distances the FOV is wider than reported.

But don't feel you have to use any specific focal length. Very interesting portraits can be made using a wide angle lens. Just do so with a purpose. For instance, a wide angle lens can be used to "stretch" perspective to make legs seem longer.

Aperture selection is critical. The key to a successful "portrait" in most cases is going to be getting the eyes tack sharp. This means using the best aperture for the lens. Typically around f/8 for average lenses, and at least one or two stops from wide open for even the best lenses. Yes, the smaller aperture is going to give you greater DOF and possibly bring the background into focus. This is not a "problem" unless you want a smaller DOF for artistic reasons. It is much better to control the BG than it is to try to minimize the BG by throwing it out of focus with a terribly shallow DOF.

Shutter Speed:

Shutter speed selection is also critical. If you want tack sharp images using the camera handheld you need a shutter speed at least three times the focal length of the lens (i.e. 1/150 for 50mm). And quite possibly faster. The ROT shutter speed is garbage, it only gets you "acceptable sharpness." Remember, people move. You'll be moving and so will your subject.
ou can get away with slower shutter speeds with exceptional holding technique, using a tripod, or using flash/strobe lighting.

No matter how much I dislike them, a tripod and a remote release are essential accessories. Get the best tripod you can afford. The remote release isn't very critical, if necessary you can just use the time delayed shutter function(timer) on your camera. Often just the tripod is enough additional stabilization.

Taking the picture:

Consider everything and do not trust your senses! They will lie to you!
Your attention will tend to be focused on the subject and you'll miss the tree growing out of their head. Your eyes will adjust and make lighting issues "ok." Your brain will "fix" perspective distortion and white balance and so many other things. You have to consider these things with intention otherwise they will be missed.

Look at every edge of the frame. Are you including distractions that could be avoided. Are you cutting off fingers or limbs unintentionally/awkwardly? Never "cut" at a joint because it will look like an amputation. 

Look at the background. Have you controlled it well? Is there a branch growing out of someone's head or an annoying hotspot? Can you reposition yourself, the subject, or both in order to eliminate it? Maybe you can move your subject further from the background in order to throw it out of focus, or maybe now you NEED to use a wider aperture.

Consider the lighting. Do you need to add some fill light with a reflector or flash? Do you need to change positions so that the shadows fall exactly where you want them?

Once you've done all of this, then it's time to capture the image you've created.

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