How to Shoot Street Portraits With Permission

NYC, 2015
NYC, 2015

If there is one genre of street photography I specialize in, it is “street portraiture.”

I love talking with my subjects, engaging with them, and focusing on their faces. If I started shooting street portraits all over again, this is the advice I would give myself:

1. Don’t hesitate

Melbourne, 2016
Melbourne, 2016

Avoid all regrets. If you see someone even moderately interesting that you want to photograph, approach them and ask for permission. It is better to ask and get rejected, than to never ask in the first place.

Assignment: Approach people who you think will say “no”


The problem in life is that we seek to avoid getting rejected— never do we seek to get rejected.

As an assignment, go out into the streets with your camera, and try to intentionally get 10 strangers to reject you. Approach people who you think look “mean” and unapproachable. Tell them what you find interesting about them, and ask to make their portrait.

You can’t stop until you get 10 rejections. Then observe and learn how hard it actually is to get 10 “no’s”.

2. Smile

Seattle, 2014
Seattle, 2014

As human beings, we are naturally suspicious of one another. In prehistoric times, one wrong look could have meant life or death.

However we are fortunate in today’s world— we won’t get killed by a neighboring tribe if we give them a wrong look (unless, unfortunately, you live in some ghettos or crime-ridden areas).

For the most part, street photography is tame. What is the best way to make your subject feel more comfortable? Simple — just smile.

In psychology, there is something called “mirror neurons”. The concept is that as humans, we mimic the behavior of others. Therefore, if someone smiles at you, you are genetically pre-wired to smile back.

There is nothing better than a smile. Better yet, even a smile from a stranger.

A smile will elevate your mood, make you feel more confident, and connected with society. Most people (it seems) walk around with a frown on their face by default (myself included). But whenever I encounter people, I try to give them a huge smile whenever possible. And that shifts their perception of me. What was initially a suspicious look, turns into an equally-enthusiastic smile.

Assignment: Click, smile, and say “thank you”

NYC, 2016.
NYC, 2016

For your assignment, if you want to shoot candid street photos, just take a photo of a stranger, click, smile, and say “Thank you.”

Then afterwards once you’ve caught their attention, approach them closer, and ask for permission to make their portrait.


The benefit of this approach: you get both a candid photo, as well as a portrait with permission. This helps you “kill two birds with one stone.”

3. “Make” a photo, don’t “take” a photo

NYC, 2016
NYC, 2016

The words you use matter. Especially when it comes to shooting street portraits.

For example, ask yourself, what is the difference between these two questions:

  • Excuse me sir, do you mind if I take your photo?
  • Excuse me sir, do you mind if I make your photo?

For me, “take” sounds forceful. It seems aggressive. It seems suspicious.


However “make” is more curious. It sounds more creative, open, and collaborative. Many Europeans say “make a photo” (not take a photo — perhaps this is what makes a lot of European photographers more creative than American photographers).

4. Make a “portrait”, not make a “photo”

Downtown LA, 2015
Downtown LA, 2015

Not only that, but change the word “photo” into “portrait”.

To continue from our past example, what is the difference between:

  • Excuse me sir, do you mind if I make your photo?
  • Excuse me sir, do you mind if I make your portrait?

To me, “photo” sounds like you just want to take a snapshot. A “photo” is something you just upload to Facebook. A “photo” seems unintentional, and perhaps a bit touristy.

However a “portrait” sounds more intentional, artistic, and considered. Artists paint portraits. And very few people have proper “portraits” of themselves.

Assignment: Shift your vocabulary

Downtown LA, 2015
Downtown LA, 2015

So for your assignment, when it comes to shooting street portraits, change your vocabulary.

Don’t say “take” a photo— say “make” a photo.


And don’t say make a “photo”— say make a “portrait.”

Try experimenting this approach with your subjects, and see how they respond differently.

5. Make your subject part of the portrait-making session

SF, 2016
SF, 2016

I feel the most beautiful part of shooting street portraits is how you can collaborate with your subjects. You can make them part of the portrait-making session. You don’t just steal their soul by taking a quick snapshot, and running away.

How do you make your subject part of the portrait-making process? Some ideas:

  • Ask your subject: “What is your good side?”
  • If your subject is feeling stiff, ask them to “jump up and down” (this will make them laugh, and allow some blood to flow in their body)
  • After making a portrait of your subject, show them your LCD screen and ask them which version they prefer the best
  • Offer to email them the portrait, or perhaps even print and mail it to them

Assignment: Have your own portrait made

Downtown LA, 2011
Downtown LA, 2011

I learned this assignment from Sara Lando — if you want to learn how to make your subjects feel more comfortable, learn how to be on the other side of the camera.

That means, hire a professional photographer to make your portrait.

Learn how they make you feel comfortable. Figure out what makes you feel uncomfortable. Then treat your subject how you would like to be treated (or how you don’t want to be treated).

6. Compliment your subject

LA, 2013
LA, 2013

Nobody hates being complimented. As humans, we are vain, egotistic, and into ourselves.

I love complimenting others— because it is free. And it uplifts, encourages, and makes people happy.

What you don’t want to do is give people false or fake compliments. People have a good B.S. meter — so always make sure your compliments are genuine.

But the key is to tell your subject why you want to photograph them. The reason you approach a subject is because you find something unique or interesting about them. So don’t be shy — compliment what you find interesting about them.

Assignment: Compliment everyone for one small thing (for an entire day)

Istanbul, 2014
Istanbul, 2014

For an entire day, compliment each person you meet. It can be small — compliment them on their earrings, their tattoos, their haircut, their outfit, their smile, their friendliness, or something else.

Make it a habit to compliment others. It will uplift them, uplift you, and help you build a stronger bond with them.

7. Hang out with your subject longer than you think you should

SF, 2016
SF, 2016

Most people are lonely, and lacking human contact. Even in big cities— we are constantly surrounded by people, but we feel alienated. Most of us just want someone to talk to, and share our life story with.

Yet we make the mistake of thinking that everyone else is always busy, and hates to talk. The truth is, we love to talk, socialize, and be human.

The mistake we also make in street photography is that when we approach a stranger, we want to quickly take their portrait, and move on. Because we feel guilty for “wasting their time.”

Shift your perception. Think that you are adding value to their lives— that you are making their mundane days more interesting.

Think about it— if you approach a stranger to make their portrait, compliment them, and chat with them — you will not only make their day, but you will have a great story for them to tell their friends and family.

For example, I was once making a portrait of this amazing woman, and someone called her. She picked up her phone, and said, “You wouldn’t believe what happened to me! I was just walking in the streets, and this strangers approached me to take my photo! He thinks I’m someone famous or something! Haha!”

There are millions of people out there — by singling out one individual — you are telling them that they are unique, special, and one-of-a-kind.

Assignment: Shift your perception

London, 2015
London, 2015

Approaching a stranger to make their portrait is a compliment. Keep that in mind.

Also when possible, try to stick around with your subject as long as possible. Keep asking them open-ended questions, and make portraits while they’re talking. When shooting street portraits, try to take at least 10 photos. Some of my best photos required me to take nearly 100 photos of them.

8. Ask your subject open-ended questions

New Orleans, 2015
New Orleans, 2015

Going to the prior point— sometimes you approach strangers to make their portrait, and they say “yes.” When they say “yes” — they often ask you, “So, what do you want me to do?”

As a default answer, I will tell them: “Can you just look into the lens, and don’t smile?” This makes the photo look more natural.

What I also like to do is to ask them open-ended questions like:

  • “What is your life story?”
  • “What are you up to today?”
  • “How have you seen this city change over the years?”

The benefit of asking open-ended questions is that your subject goes into “story-telling mode”. And when they do, they forget about you. You disappear into the background. And this causes your subject look more natural.

Assignment: Click while your subject talks

SF, 2016
SF, 2016

Try to make photos while your subject is talking.

Try to capture their mouth moving, their hand gestures, or body language. Try to get photos of them with eye contact and without.


“Work the scene” and try to make as many different versions of the photo. Often when you make photos while people are talking, they are more fluid, vibrant, and dynamic.

9. Look for a clean background

SF, 2016
SF, 2016

One of the photographers who have inspired me the most is Richard Avedon. He was famous for photographing his subjects against a simple white backdrop.

This allows you to put 100% of your focus to your subject’s face.

One of the mistakes a lot of us make in street portraits is that the background is distracting or messy. You might find someone interesting in the streets, and just quickly snap a photo of them. But you might have a distracting pole sticking out of their head or shoulder, messy trees, or power lines.


So when you approach a stranger to make their portrait, and they say “yes” — look around, and ask them to move against a simple background. You can explain it to them too — say, “Oh excuse me, the background here is pretty messy. Do you mind standing in front of this simple white background here on the left? It will make a better photo.” This will make your subject more willing to cooperate. And surprisingly, I have never met a subject who said “yes” to my request to make their portrait not want to move against a simple background.

Assignment: Find clean backgrounds

Berkeley, 2015
Berkeley, 2015

My suggestion: when you’re out shooting in the streets, try to first identify a clean background. It can be a gated background, a brick wall, or just a clean white/grey/single-colored background.


Then just wait for your subjects to come to you. Then when they come close by, ask your subject to make a portrait of them against the background you’ve identified.

10. Capture a hand-gesture

New Orleans, 2015
New Orleans, 2015

I generally find street portraits of just faces a bit boring. For me, my favorite street portraits is when you get an interesting hand-gesture or body-language.

To get your subject to make an interesting hand-gesture, comment on something near their face. You can try the following:

  • “I love your glasses! Where did you buy them?” (most people will start playing with their glasses, that is when you start clicking).
  • “Wow your beard is so long! How long did you grow your beard?” (most people will start playing with their facial hair, which is an interesting hand gesture, then you start clicking)

1-contact-nola-2 1-contact-nola-1

You can also ask them to just pose for you a certain way, and ask them to mimic you. Some interesting hand gestures:

  • Fist on the chin
  • Scratching forehead
  • Hand on the side of the face

To build upon this, you can also ask your subject to look in different directions (ask them to look up, down, left, and right).

And to top it off, you can even try to provoke a funny reaction from them. For example, ask them to give you a big laugh and start laughing really loud yourself. Say, “HA HA HA!” and usually people will laugh (back at you), and that is when you start clicking.

Conclusion: Learn to be comfortable in your own skin

Hayward, 2016 #cindyproject
Hayward, 2016 #cindyproject

Shooting a street portrait (imho) is more difficult than shooting traditional “candid” street photos.

Why? Because when you shoot a “street portrait”, ask for permission, and interact with your subjects— it takes a lot of guts. It takes great courage. You need to step outside of your comfort zone, and put yourself out there.

It is easy to snap a photo of a stranger without permission, and move on.

It is hard to empathize with your subject, bare your soul, and make yourself naked.

Garden Grove, 2016 #cindyproject
Garden Grove, 2016 #cindyproject

The last piece of advice I have you when it comes to shooting street portraits is to shoot with your heart. Do so openly, with a huge smile, and don’t hesitate.

Also know that the skills of approaching strangers and making their portrait will help you in all forms of your life. You will become more confident, more courageous, and hesitate less (in personal life, in business, and with your relationships).

Berkeley, 2016 #cindyproject
Berkeley, 2016 #cindyproject

Lastly, are you comfortable in your own skin — and being on the other side of the lens? Learn to first be comfortable with who you are, before you decide to go out and photograph others.

Be strong, confident, and valiant!


Keep learning about street portraits/street photography

To learn more about shooting street portraits, check out my free ebook: “The Street Portrait Manual.”

Also check out Street Photography 101 >