I belive street photography is the best way of improving and building confidence in the field of photography, let me share with you some tips on Howe to start with street photography.
1. Try using lenses which do not exceed a maximum focal point of 50mm. (getting close to your subjects makes you bold)
2. Try taking to strangers and convience them to let you take a photograph of them. (talking to strangers will help you open up and make you feel more confident)
3. if you cannot talk to strangers just yet, try taking their pictures from a different angle without them knowing.
4. Don't dress up like a stalker or a convict. (yes try to keep it decent)
5. Remember to smile. ( they will probably be wondering what you would do with their pictures, so make them feel safe always smile and have a little conversation)
6. In the beginning you should be looking for quantity of pictures taken.( the more you click the more you understand the technical stuff about photography)