Let's be honest here: Sometimes it just works, almost randomly. You take a photo of someone, and it happens to turn out great. This is usually the case when you're photographing someone who feels comfortable in front of the camera. They smile, they're relaxed, and it's easy to see it on the photo. You then have a photograph that creates the impression (true or not in absolute* terms, it's a question mark!) that you have captured with your photo a shiny happy person.
*Psychology digression: It's easy to be fooled by smiles. A person who smiles and is jolly all the time is not only creepy, but probably hiding something under the surface. Needless to say, getting a genuinely sad photo of someone like that, will probably be a masterpiece
Most people though are not like that, they feel goofy, uncertain, awkward in front of the lens. It's your job to help them overcome this and not pose, but rather just be in front of the lens.
You might be wondering what this long introduction has to do with urban portraits. Well, I'll tell you a little secret*: People dislike being in a studio. People don't want to be looked at by a photographer and couple of assistants, they don't want softboxes and blinding lights, they don't want backdrops that mentally block their escape. People want to break free!
*heck, it's actually a business secret! Our photography business is all about "getting out of the studio" :D
So, urban portraiture is something that can really help people feel more relaxed. Don't think of it in terms of "smiling". A good portrait is not necessarily about smiling people. It's all about the essence (of course the result must be something that appeals to someone), but it must be genuine. Between genuine and melancholic, on the one hand, and fake and smiling, on the other, I'd pick the former any day.
1) Mobility is the Key
Forget large softboxes and reflectors, forget tripods, forget stands. Find ways to go around those, somehow. My favorite setup for urban portraits is my trusty D700 with a Nikkor AF-D 50mm f/1.8, plus an SB-800 with a small diffuser. It's very capable, it's light and allows me to get into awkward positions, and it never gets in the way. You might think 50mm is too short for FX portraiture. It isn't. For some things I might wanna bring an 85mm or 105mm short tele, but generally speaking just the 50mm would be fine. Rule of thumb: One camera, one lens on it (optionally one additional in your pocket; if it doesn't fit in a jacket/small bag pocket, don't take it), one flash.
2) Play with Light
Photography, like art in general, is about showing reality in alternative ways. You must find ways to use the light in ways that enhance this reality. If you have an interesting person looking at you, why limit yourself and them with a boring, out-of-the-picture snapshot in overcast sky. Dull, grey, uninspiring. Show some drama instead. Just an idea to get you going (experiment yourself with more): Underexpose the ambient light by 0.7 (or even 1.0, depending), then illuminate your subject with diffused light from the flash
3) Play with Angles
Many DSLRs have viewfinder grid lines or even virtual horizons to help you achieve a perfectly straight horizon. That's for lakes and sunsets, forget about it with portraits. Tilt baby, tilt! Add dynamism in a scene by tilting the camera 30 degrees. The world is always steady, use your photography to change things a little.
4) Location
Don't overthink that. It's not about finding some extraordinary location, something unique or something nobody else has discovered. On the contrary, it's about finding the unique in the superficially mundane. Some abandoned cars, graffiti on the wall, a garage in a working class neighborhood... These are locations worth visiting, not some luxurious lounge in some 5-star hotel.
5) Interact with the Person You Are Photographing
The last tip is the most important one. It has to do with a core issue in portrait photography - we come back to the introductory point. Don't be silent, and don't be clinical about what is happening. Talk to the person, if you don't know them well enough to ask personal questions, ask them their opinion about what they see around them. Make meaningful conversation about your environment. See the sublime magic whether it is a simple alley or passing cars, and find meaning in it. Share it with the other person.
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