Most of the photography I've done since i started shooting about 6 years ago would be considered outdoor or nature photography. I thought it would be fun to try some street photography. To a purist, street photography is done in large cities (L.A., New York, London, Paris) with a black & white film camera, preferably a rangefinder. Some photographers including Chris Weeks, a Los Angeles street photographer, don't consider you a street photographer unless you shoot with a Leica camera. Well, being a non conformist, I'll do it my way, thank you very much. Anyway, Chris is an excellent photographer and I figure he is just making a point - probably a good one.
After getting some feedback from my friend Carl Garrard (who often does use a rangefinder), I decided to buy a Canon S95 point and shoot since my primary camera, a Canon 5D mkII is a bit large for street photography. My first attempt was a Laguna Beach a couple of weeks ago. As you can see, I'm not a purist and I'll do some in color, some B&W, all in digital and most with a point & shoot. It's a fun but tough genre.

I have no illusions about becoming a Henri Cartier-Bresson (in my opinion, the best photographer of the 20th century), Garry Winogrand or Bruce Gilden. It's best not to be self conscience. My advice based on limited experience is to keep in mind that what you are doing is both moral (everywhere except places where people expect privacy), legal (at least in the U.S. although not in most of Europe) and you must keep your focus on the world you are watching and not on yourself. Also, don't take compromising photos of people; that's rude.