These tips apply both to film and digital shooting. Either which you’re shooting with, you can use these techniques to approach your subjects. I’m assuming that you’re using something like 28mm, 35mm or 50mm lenses, that are pretty standard in street photography. Most of these techniques don’t apply well to tele-lenses, but otherwise they are well proven to work, no matter what gear you use, even though cameras of the smaller and more discreet size are encouraged.
1. In and out in five seconds
Very simple technique that requires mainly just guts and determination. You’ll need to have your camera ready. Pre-meter and pre-focus — be ready in every way, as soon as you detect the subject. Without hesitation, just walk to the subject, take the shot and walk away. Pre-visualise the shot in your mind as you go in. Don’t stop to fumble with the camera or to hesitate. Do it all in one well determined motion. You might get noticed or you might not. This is not the easiest technique, because it requires some mental toughness, but very rewarding once you get the hang of it. You’ll get away with your fear of photographing people for sure.
2. Stealthy hip shot
Almost the exact opposite to the previous technique, is a stealthy hip shot. You’ll need to be sufficient at zone-focusing to get sharp images without looking through the camera, but otherwise hip shots are a pretty sure way to get close to the subject without anyone noticing or causing discomfort to anyone. I’d prefer zone-focusing over auto focus (if you happen to use one) because it’s faster and more reliable at hip shooting. A quiet camera definitely helps a lot to maximise stealthiness. Hip shots works, but in my opinion, they are not as satisfying as images you’ve framed through the viewfinder. You’re relying more on your luck than your composing skills. On the other hand, it’s fun to get random compositions that surprisingly often happen to work just as well. Good way to get away of your composition mannerism.
3. Pretending to shoot something else
Sometimes you don’t need to try to be invisible. You can just mind your own business and even let yourself to be noticed. If you happen to have a wide angle lens, you can frame the subject closer to the edges of the image. It will look as you’re taking a picture of something else, because you’re not pointing the camera directly to the subject. The subject usually doesn’t realise that they are in the frame, because most people don’t know how wide angle lenses work. You’ll need to be close though, but just keep your cool and don’t make contact with the subject even if they notice you.
50mm lens works just as well, but it has a much narrower field of view. In that case pretend you’re photographing something or someone behind your subject, because now you are pointing the camera to the subject more directly than a wide angle would allow. The most important thing is to completely ignore the actual subject and create the illusion that you are completely oblivious to their existence. If you get an eye contact through the viewfinder, just keep doing what your doing and don’t lift the camera off your face. When/if you lift the camera off your face, keep looking pass them as if you are looking the building or street sign next to them.
4. In your face
This is the most straight forward and simple approach. If you don’t mind getting noticed, you can just take the photo, without pretending to shoot something else or without trying to be stealthy. Sometimes you can just go and do it.
5. Talking to them
Engaging a conversation is a popular technique, but the one I use the least. When I learn how to be more social, I’ll definitely start to favour this technique more. Engaging a conversation is almost a sure way to get good photos, but what I don’t recommend is asking someone random whether you can take their picture. At that point it isn’t candid anymore, but if you’re going for a street portrait etc. it’s not an issue of course. Instead, I’d incorporate a chatter into a candid work, perhaps by starting the conversation completely about something else. I wouldn’t give the impression that I’m interested at the person him/herself per se. Conversation allows you to enter a very close range. But how to proceed from there to the actual picture taking, is a harder question. You may need to resort to a stealthy hip shot, if you have a quiet and discreet enough camera. Getting caught though may be somewhat awkward. Or maybe you can ask whether you can take of his/her tattoo or some other thing that caught your eye. Conversations can lead to surprisingly fruitful photo opportunities.
EDIT: In case you’re interested, I’ve written another article on the same topic, covering five additional approaches as well, called Five Additional Methods (part 2) on Approaching Your Subject in Street Photography.