Or at least as much as you can. If you really want to improve your Street Style pictures, the most important thing you can do is to actually go out and shoot. See which photos you like or don’t like, learn from them, and apply what you’ve learned the next time you’re out shooting. Street Style is all about practice, practice, practice. The point is that eventually, when you edit your photos, you'll find the ones you do like, get rid of the ones you don't like, and you'll start to train your eye towards developing a personal style within the context of Street Style (which, admittedly, has more limitations inherent to it than just about any other style of photography).
Don’t be Afraid not to Ask
Sometimes the best Street Style photos are the really candid ones–the unasked for ones when you catch a person at their most honest and unguarded. Remember that once you ask someone if you can take their photo, they become self-conscious and will project an appearance of themselves instead of showing you who they really are. It can be tough to put a camera in a person’s face and take their photo without asking, but you’ll eventually become more comfortable doing it.
On the more technical side…
Choose the Right Tools
Not every lens is right for Street Style. I’ve found that it’s best to stay away from wide angle lenses, i.e. your 16mm, 24mm, 28mm, and 35mm lenses. These lenses can cause distortions and an effect known as keystoning, which causes straight lines in the frame to converge at the top or bottom of it unless your lens is perfectly parallel to your subject. These effects aren’t necessarily bad, but they aren’t particularly flattering to human subjects (or their clothing). When I shoot Street Style I usually use a 50mm lens, which is regarded as “normal,” close to the perspective of the human eye, and generally without wonky distortions.
Focus on Your Subject
This seems pretty obvious but let me explain. As I said I usually shoot with a 50mm lens and set it to at an aperture of f/1.8 to keep the background out of focus and the subject in sharp focus. In order to achieve perfectly crisp focus at that f-stop, I NEVER MANUALLY FOCUS. The reason for that is because DSLRs’ focusing screens are not designed to accurately show focus at such low f-stops and compact cameras’ screens are still fairly inaccurate unless you’re zoomed all the way in, which takes too much time. What I do is I set my auto-focus point (refer to your camera’s manual for info on this) to the exact center, aim at the subject’s chest area, and voila! Perfect focus every time. Don’t leave your camera to its own devices with all of the AF points activated: it will work out an average focus for the scene which is usually not at all what you want.
Hopefully these tips were helpful for you, next step: go out and shoot!