Mastering the Art of Street Portraits

Street Portrait Photography
When done best, street portraits will often feel like candid moments, where you can feel a connection to what a person might be feeling or thinking.


The Magic of Street Portraits

When many think of street photography, they typically think about traditional candid photography. But street portraits are a huge aspect of the genre.

If you look through the many greats of street photography books and projects, you will see that portraits take on a huge piece of telling a story of a place or an idea.

Sometimes candids are preferable but often they’re not. Street portraits can be the best way to describe a person, to share the psyche of an area.

And depending on where you live, particularly in quieter and more suburban areas, it can be very tough to take candid photographs, so street photography portraits can be your best bet.

Here are some tips to take you to the next level with your portraits.


1. Just ask

Street Portraits

This may seem like such a simple tip, but it’s so important. Especially when you are beginning, it can be very nerve-wracking to stop a stranger outside and suddenly ask for their portrait. Rejection can be tough and it can feel a little creepy at first.

However, this will quickly fade the more you do it. The goal is to create a connection with someone and the other people will feel that as well.

You will find that you will have many more wonderful encounters than rejections, and even the rejections won’t be so bad. You will have the ability to make peoples’ days with your camera, to flatter them, to break their routine.

Other people are looking for a connection just as you are. So force yourself to do them, and you will quickly find it to become both easy and exciting to do.


2. Not just the flashy – Look for people with a special quality to them

Street Portrait Photography

One mistake that is commonly made is that photographers only look for the flashiest people – the people who want to stand out when walking around.

Many of these people you will certainly want to photograph, but they are only a portion of the people out there and you will be missing out on everyone else.

Seek out people with a special quality. Over time, you will be able to figure out what that is and who has it. Look for ordinary everyday-looking people, people with interesting emotions on their faces, or people who just look open to having a connection.

The people in your photographs should be a broad representation of the place or story you are trying to tell.


3. Family, friends, and neighbors

Street Portrait Photography

Don’t only rely on strangers. Neighbors, friends, acquaintances, and family can make for fantastic subjects.

The people you are around the most, the people you know the best, are the ones who can give you the best opportunities and be the most comfortable around you, so keep an eye out for them.

The key is to not force these portraits too much. Wait until you find them doing interesting things or in the right place and then go to take a portrait. Make it a natural moment – these portraits need to feel and be real.


4. You owe them a good portrait


I often see people ask for a portrait, take a quick one, and then slink off. While it’s necessary sometimes to make it quick, that’s not the best way to go about this.

If your subject is giving you the time to make a connection, you owe it to them and yourself to take a good portrait. Talk to them for a second. Think about the background, lighting, and find the best angle. Give them a word of advice.

Take a few shots and make sure they feel comfortable to the best of your ability.

You’ll often find that it’s either the first or last shot that is the best (so make sure to pay particular attention when taking the first few photographs). With some subjects, you’ll take three or four photographs and it’ll be clear that you got the shot or that the subject is not going to improve from that.

Other subjects you will have to talk to and work a bit to get them to become comfortable and reveal themselves.


5. Talk and ask questions

Street Portraits
Street portraits do not have to only be done outdoors.

Street portraits are about connections, so make that connection when you can.

For me, half of my portraits are quick-enough encounters. It will be clear when that is the best strategy. But for the other half, taking the time to talk to them for a bit is the way to go, both for taking the best portrait you can and for creating a great experience for you both and having a good time.

It’s fascinating to learn about people as you photograph them.

Think about questions ahead of time that you can ask them. Depending on how you read the situation, it can be simple talk like talking about their clothing or how their day is going, or you can get deeper. Ask them what their dreams are, what they wish they could be doing right now, or to think about something that’s been on their mind as you photograph them. This often can bring out some great emotion.


6. Spend some time with them

Street Portrait Photography

Taking this a step further, occasionally you will come across a fascinating person, with which it’s clear you can spend more time with them.

In these cases, take as much advantage of this as you can because they don’t happen very often. Talk about their lives, ask questions, really get to know them.

Better yet, ask them if they have a favorite place nearby where they would like their portrait taken.

Some people will even show you around their homes, which can be one of the best places to take a portrait and get to know someone.

I know this sounds like a lot at first and a big step from just stopping people on the street for a quick portrait, but as you progress and get more comfortable, as you ask more people, these situations will arise, and they will absolutely make your week.


7. Tell them you want them to look natural

Some of your subjects will go into the perfect, natural pose right away. But others will stiffen up and not be sure what to do. Others will give fake-ish smiles or a thumbs up or peace sign.

One of my favorite street portrait tips is just to tell people what you’re trying to go for. Tell them you want the portrait to look and feel as natural as possible – that they should try to stand and act as if I’m not shoving a camera in their face. Maybe they feel like look at the camera or away, but it’s up to them.

A portrait like this is a collaboration, and the more they know that the better they will do.


8. Wait for them to let their guard down

Street Portrait Photography
This was a street portrait, but to capture a candid feeling moment I placed my camera down for a second to pretend to take a break while talking to her, giving her a chance to let her guard down.

Within slightly longer portrait sessions, you have the ability to disarm people and take them out of the feeling that they are being photographed.

This is why having a conversation is so important. When you get someone talking the session becomes a fun conversation instead of a session – they’ll often somewhat forget what is happening and you can watch their expressions as they carry on.

Sometimes I will lower my camera to continue the conversation so that they really don’t feel under the spotlight. I will then wait till they look right and bring the camera up to take a quick photo or two, and then back down to continue talking.

This is a very comfortable way to photograph them in which they’ll start to forget about the camera.


9. Eyes, facial expressions, and body gestures

Street Portraits
I pass these men constantly and a few weeks after taking this photo, I framed and delivered one to each of them. It made their day.

The eyes and facial expressions are the keys to a good street portrait. Everything you do is to get them to give you the right expression.

I always look at the eyes and pay attention to what they seem like they are feeling. It’s vital to do this and to try to capture the portrait at the right moment when these emotions are being revealed, although it can be difficult because sometimes you just get a split second of a powerful look and you have to act quickly.

Similarly, gestures in the body can reveal just as much. Is the person tense or loose? Both can make for fascinating portraits.

When you tell someone to try to stand in a natural way as if you weren’t there photographing, this will often help their body to open up and express itself, as opposed to just straightening and stiffening up for the camera.


10. Think about the background

Street Portrait Photography

Many photographers will focus right in on the face and blur or forget about all of the surroundings. And in many cases, this will be the right choice for the photograph.

But often it’s not.

Street portraits need context – and a good background can set the stage for the portrait and show a fascinating environment that helps to further the story.

So think about where you want the person to stand. Look at the details in the background. And think about whether you want a closeup of the person’s face, part of their body and the background, or if you want to back up and make them a smaller part of the photograph with a lot of background.

There will be a time and place for each of these options.


11. Study the great street portrait photographers


One of the most important aspects of improving your street portraits is to look at the work that’s been done by others.

It will open you up to many different possibilities and styles, and it will make you much quicker on your feet when out there doing your own portraits.

Some photographers that I suggest looking at are Alec Soth, Diane Arbus, Joel Sternfeld, Mark Steinmetz, Mary Ellen Mark, Walker Evans, Niall McDiarmid, and Matt Black.

Now that you’ve read this, the next step is just to get out there and ask! It will get so much easier and turn into a lot of fun after just a short while.

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