Taking street portraits can be daunting for a photographer. For most of us it's not easy to walk up to a stranger on the street and ask to take their photograph. Even after Humans of New York and similar projects it's still relatively unexpected to be approached on the street, especially in a lot of cultures where most interaction is to buy or sell something, or maybe ask directions.
Don't let that put you off though. It's an incredibly rewarding experience, a great way to meet people, an opportunity to give a gift to someone you might never meet again and it should be a part of the repertoire of a good street photographer. There are also a few things you can do to make your experience of street portraiture more successful.
Don't try to stop someone who looks like they are already in a hurry. People with some time on their hands are more likely to be relaxed and happy to talk. So if you notice someone who looks as if they are waiting for something or casually browsing shop windows or generally taking their time, they could be a good person to approach.
I also have a theory about hats. It hasn't been verified as far as I know, but my theory is that someone wearing a hat is more likely to enjoy being photographed. Hats are often worn for style more than function, so the wearer probably takes pride in their appearance and might like to show it off in a photograph. As I say, it's just a theory...
Sometimes the choice is made for you. You notice someone and there's just something about them that makes you want to take their portrait. You might only have a moment to decide whether to approach them. I've missed a few opportunities because I haven't had the guts to approach someone, and I'm always kicking myself afterwards. Be ready and go for it.
Have a plan
You can approach this in two ways. Either plan the image (such as the location) in advance then look for a suitable subject, or if you see a subject that you want to approach, quickly work out what kind of shot you want to make. Ideally you want to consider the backdrop, lighting and composition. Your subject will expect some direction so be ready to at least tell them where to stand and where to look.
In the shot below I noticed that Alexis had a hood on her jacket so I asked if she would mind putting it up for a couple of shots. Then I simply asked her to relax her mouth so that her expression would look more natural.
Be friendly and confident
The worst thing that's likely to happen is that the person says no. In most circumstances, a candid shot without asking permission is more likely to cause concern than simply asking if you can make a portrait of someone.
So try not to be nervous. Explain that you're a photographer and that you're working on a project, or taking some street portraits, or documenting life in the city, or whatever it may be. Then just ask if they would mind you taking a few photos. You might want to chat to them more as you take the shots. Ask their name and a little about themselves. Just being friendly will help them relax and it might give you ideas to incorporate into the portrait too.
It could be a compliment to someone that you want to take their photo, so try to make sure it comes across that way. For the image below, I complimented this gentleman about his dog and asked if I could photograph it, and he immediately picked it up so that they could pose together.
Be willing to send them the photo
Rather than take an email address from someone, I prefer to give them mine on a business card. That way they can see my website and get in touch if they would like the photo. Some do get in touch and I thank them again for their time and send them a high-resolution file. If you say that's what you'll do, make sure you do it. Then it's a positive experience for everyone and you've been able to give a gift to a complete stranger. Not a bad way to spend a little time practising some photography skills.