There is one subject above all others in street photos I try to include whenever possible. It’s one that can turn okay images into amazing street photography portraits. I’m talking, of course, about people. Including people in your street photos adds feeling and depth, and it brings the images to life.

Frequently, during the photography workshops I run, I teach people a skill that has nothing really to do with their camera. I teach them how getting outside their comfort zone can add a whole new dimension to their street-style documentary photography.

Here are five tips to help you get outside of your comfort zone and elevate your street photography.

Market Porter Step Out Of Your Creative Comfort Zone to Take Your Street Photography to the Next Level
© Kevin Landwer-Johan

1. Push Past Your Anxiety

Typically, photographers are reluctant to connect with subjects in their street photography portraits because they are anxious about imposing on people. I’ve found that very often the opposite is more of a reality.

Asking someone if you can make a portrait of them will generally make their day. You are paying them special attention. You are showing respect to them for asking permission first. You are brightening up their world.

Changing your mindset away from the negative impact you think you’ll have if you ask, will give you confidence. Once you begin to practice approaching people it does get easier. Developing a consistent style in the way you ask people will increase the number of positive responses you receive.

Vege Man Step Out Of Your Creative Comfort Zone to Take Your Street Photography to the Next Level
© Kevin Landwer-Johan

2. Pick The “Best” People for Your Street Photography Portraits

Observing people is important before approaching them. Often you will be able to spend a little time watching someone without them being aware of your presence.

Discern whether or not they look like they will want their photo taken. Are they open or approachable looking? Or is their body language closed and guarded? Seek out people who look confident in themselves and leave out the ones with a scowl on their faces. But be ready to be wrong.

Flower Seller Step Out Of Your Creative Comfort Zone to Take Your Street Photography to the Next Level
© Kevin Landwer-Johan

During one of our workshops, I would regularly see this guy working at his shop in the flower markets (see the image above). He would always wear a black t-shirt and he had lots of tattoos. He never seemed to be smiling much, either. I wanted to photograph him for a long time before I found the confidence to ask. But I am glad I did.

Every time I pass by, we chat. Sometimes, he gives flowers to our workshop participants. I made a friend because I stepped outside my comfort zone. I also have a number of portraits of him, which I have printed and given to him as a gift.

It’s not always easy to pick people for street photography portraits, even with years of practice. But, if you never try and ask, you will never know.

Samlor Rider Step Out Of Your Creative Comfort Zone to Take Your Street Photography to the Next Level
© Kevin Landwer-Johan

3. Take Your Time

Be committed. It will take time and practice, but even the shyest people can make a go of street photography. I speak from experience. As a young man, I was painfully shy. Talking to strangers scared me.

I realized if I wanted to keep the job I had landed in the photography department of the newspaper, I would have to overcome my fear. I often had to photograph people I did not know. The only option I had to stay inside my comfort zone was to leave this job. I did not want to do that.

Over time, as you begin to talk with people you don’t know and take their photos, you will build confidence. You will not only find that many people say yes, but also that they enjoy the process, too. As you get more comfortable, your photography will also improve.

Loikaw Market Friend
© Kevin Landwer-Johan

4. Plan to Succeed with Street Photography Portraits

Work up to photographing strangers in the street. If you’re not used to taking photos of people, start with someone you know. Make portraits of them regularly for a month or more. You will begin to develop your manner as you photograph them.

Paying attention to your subject and not your camera is vital. Try to avoid always looking down and fiddling with your camera settings. Instead, talk with the person you are photographing. Make eye contact and connect with them. Be warm and friendly, and your subject will reflect this back to you.

Once you’ve practiced, head out to the streets. Make a commitment to yourself not to stop until you have a set number of street photography portraits. Try and make it three or more. Be aware of how you are feeling and what you are thinking while you accomplish this challenge. Remain positive, even if some people give you a negative response.

Sunday market Vendors
© Kevin Landwer-Johan

5. Start A Project

Telling people you want to take their portrait for a project you’re working on can often bring a higher rate of positive responses.

Begin to build a body of work around a concept or theme. To keep yourself motivated, aim to have your images presented in a gallery, or in your local library, or even just on a photo-sharing website. This will give your subjects confidence in what you are doing and give yourself a greater sense of purpose for your photographs.

Whenever you can, take prints back to the people you photograph. More often than not, this will bless them (or at least make them happy) and possibly open more opportunities for your photography.

Person holding up a Portrait Print
© Kevin Landwer-Johan


At the end of the day, like with most things, you must practice, not only using your camera but also in approaching and communicating with people. Don’t get me wrong; you should know your camera well and understand the settings you need to use so that when you approach someone you can pay attention to them, not your camera.

Old Woman With Flowers
© Kevin Landwer-Johan

Lastly, don’t give up. If you don’t persevere, you will remain inside your comfort zone and your street photography will not be as good as it could be. Once you have learned to get comfortable being uncomfortable, you will find the boundaries of your comfort zone expanded and your street photography much improved.

Make a start today. Ask a friend, or even a stranger, if you can capture their portrait for your new project.


What are some other tips you have for approaching strangers to feature in your street photography images? Please share your tips in the comments below.