I'm envious of the people who are good at street photography. It's something I've never felt comfortable doing. I think it's because I'm somewhat of an introvert, so sticking a camera in someone's face to take a photo or even standing in the shadows and possibly getting noticed while firing the shutter makes me uneasy.
The closest thing I come to doing street photography are the silhouettes I shoot of people walking and playing on the beach near where I live. I enjoy going for a stroll on the beach late in the afternoon, the magic hour, just as the sun begins to set low over the Pacific. I almost always have a camera with me. I find that if I put my subjects between me and the water, most everyone just thinks I'm taking photos of the ocean and rarely pay me much attention.
I've made some of my favorite photographs this way. Shooting black and white film. Exposing for the backgrounds rather than the people I'm shooting. Here are some of my favorites. Cameras used were Nikon F2, Leica M2 or M3, Contax RX or Nikon FM2n. These are from a variety of film stocks: Kodak Plus-X, TMax 100, TMax 400, Fuji Acros and Kodak Tri-X Pan.