Similar to nvitalephotography's posted image, my first foray was this shot:



From my vantage point 7 floors up I felt a bit more confident snapping strangers, but since then I've been happier getting closer. The 15-85mm is fine if I use a silicon wrist-band as a rudimentary zoom lock, but it's quite intrusive being a medium sized lens on a medium sized SLR. I think I'll have much more confidence with the 35mm f/2.0

Other than that I find shooting from the hip is surprisingly easy. Anywhere shorter than 35mm and you can afford to be a bit lax with your aim.

Some people say they find it easier with a 200m lens, but tbh I think I'd find the thing attracting far too much attention.

The other thing that really helped me was going on a photowalk with some more accomplished street photographers, you have a lot more confidence when in a group wandering around, especially when it's clear you're photographers snapping away at everything. I also learnt to just worry about getting the shot, the story of the image matters a hell of a lot more than the technical accuracy, like this one: