Street Photo Mood

Tips for capturing striking portraits in the streets

The Henry’s team linked up with New York-based street photographer Jason Roman, aka @Stockezy, to get his tips on making it easier to approach subjects to photograph in the streets. Here are his top three tips:

Street Photo Subject

Street Photography Tip #1: Start with easy subjects

Tip number one, start off with easier subjects. 

I always tell people, “don’t challenge yourself too much.” When you’re first starting out with street photography, look for people that are easy subjects like street performers, elderly people, and people who are dressed really nicely. These are the types of subjects that are a lot easier to approach and are more likely to say yes. 

The reason you want to start with easy subjects is that it will help you build up the courage and confidence you need to start approaching people that are more likely to say no. 

Street Photo Mood

Street Photography Tip #2: Consider your mood

Tip number two is to take your mood into consideration.

If you’re not in the best mood or are feeling vulnerable, don’t ask people for photographs. Approaching subjects to photograph when you’re not feeling your best can put a damper on shooting for you. 

When I was first starting out, if I felt insecure about asking people to be photographed, I would find something else to photograph that day. I’d save street photography for another day when I was feeling more myself. It’s really important to take your feelings into account. If you’re not feeling it, photograph something else. 

Street Photo Walk

Street Photography Tip #3: Know why you want to approach a subject

Tip number three is very important: Know why you want to approach a subject. 

Before I even approach a subject, I’ve already figured out why I’m approaching them. Especially in New York City, people are rushing around and don’t like to be stopped, so I have to know exactly why I want the portrait the moment I stop someone. It could be the shirt they’re wearing, the mood they’re in, or the way the light is hitting them. I always tell the subject why I want to photograph them as soon as I approach them. 

Always know the reason before you approach someone, you don’t want to be fumbling with your words and make it uncomfortable for both of you.

Bonus Street Photography Tip: Remember to have fun!

Just remember to have fun. It’s just street photography. They’re just people you’re approaching. In my experience, if you get to know the subjects that you’re photographing, chances are you’re going to capture a better portrait.

Set yourself up for street photography success

Visit Henry’s for the latest in street photography cameras and gear, including fast, compact mirrorless cameras and lightweight tripods.

What’s next

Learn more about Jason Roman aka @Stockezy

Check out Jason Roman’s street photography at and follow his journey on YouTube and Instagram.

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