There’s some debate about exactly what street photography is, and this debate also spills over into the realm of street portraiture. Many people insist that all street photography must be undirected, and the photographer should simply capture the event as it unfolds. While it’s great to be an outside observer capturing interesting, absurd, surreal or even banal scenes, sometimes it’s good to get out of the observer mode and actively participate in the scene. One of the best examples of this is the famous William Klein photograph "Gun 1." The image portrays a young boy pointing a toy gun at the camera. While this street portrait looks menacing and off-the-cuff, Klein himself said he instructed the boy to point the gun at the camera and "look tough."
So what exactly makes a street portrait? A street portrait is usually more than simply taking a portrait of someone in the street. For example, photographing a model in the street by design isn’t a street portrait. A street portrait should retain the spontaneity of street photography while capturing the essence of the person or moment.
The key to getting a great street portrait is to get intimate with your subject, which requires getting relatively close. This allows you, and eventually, the viewer of the photograph, to feel a real connection with the subject. What separates a candid photo from a street portrait is the feeling of being there with the person rather than looking at them from afar.
In order to do street portraits, it’s great to find an interesting person or group of people, as street portraits can have more than one person. Now, interesting doesn’t necessarily mean the person has to be completely wacky or off-the-wall. Look for people who have a unique style, a captivating look or a story to tell. Oftentimes, a seemingly mundane person can be interesting in their "normalcy." There are no rules to what kind of people you should photograph.
Wandering the city streets or sitting in a coffee shop that has a window facing the street or at an outdoor café along a thoroughfare are all great ways of spotting fascinating or compelling people. The key to finding subjects is that you need to put yourself in a position where you’re likely to come across a wide variety of people. Luckily, I happen to live in Austin, Texas, which is a city well known for its diverse population.