If you haven’t tried street photography yet just because you think it’s too difficult, you’re just making excuses.
Personally I think street photography is one of the most interesting fields of all photography. You have a chance to capture some truly unique moments of real life. You can capture awesome candid images anywhere, not just in the streets of the biggest cities.
You can only photograph on busy city streets
Street Photography can be done almost anywhere. Great photographers have a knack for learning how to take strong photographs in areas that others may think of as lacking content. Go to areas that you think would be terrible for photography, and try to figure out how to take a good photograph there. This is a very powerful exercise for your growth.
You need a lot of depth and many different things happening in the scene for it to be effective
What makes a photograph good is what is happening in it. Search for that first, and then you can figure out whether it will be better to create a complex image with a lot of supporting elements, or whether it will be better to just focus on the main element. It will be counterproductive if you walk out the door looking to create only images like Alex Webb. Look for interesting things and then figure out the best way to frame them.
Great street photographs are all about luck
Photography is both about waiting for these moments and about seeking them out. If you put in the time to shoot, you will come across many moments, no matter where you are. As you improve as a photographer, more moments will not occur around you, you will just get better at noticing them.
Street photography is about being bold
No matter what, you are going to have to bring yourself out of your comfort zone. You are going to have to figure out what you want your images to look like, and what you need to do to pull that off. If you want to use a zoom lens, use it because you like the look of a telephoto image, not because you are afraid to get close. If you are afraid to get close, use a light wide-angle lens, pick a spot, and let people come to you. Inch a little closer each time. You do not have to jump in there with cameras blazing to capture a good image.
Street photography is about the extraordinary
Street photography can focus on anything. It can be colorful, mundane, ordinary, or something overt. A lot of the most incredible street photography actually captures ordinary moments in ways that feel extraordinary. Street photography is about finding the extraordinary in all types of moments. Do not just sit there looking for red hair. Seek out people and scenes that fly below the radar, and capture what makes them interesting.
Source: Digital Photography School