Shooting street style seems like an easy task at hand but it can be tricky and done incorrectly. In the time I've been shooting street style, I've learned a lot of tactics that have taken my street shots to the next level. While there is no place on the internet that will teach you this, I have decided to share my learnings and hopefully inspire you to up your photo game. 1. Be patient. Unless there is an event with built-in traffic and a large crowd of fabulously dressed subjects, you will have to invest time (and patience) into getting the best shots.
2. Be selective. Don't shoot someone whose style you are not enamored by, make sure to love their style so your readers will too.
3. Don't look for brands. I feel a lot of people have a misconception of street style scouting and search exclusively for labels. Au contraire, keep an eye out for killer personal style, details, and overall look. If labels are a part of that - great, if not, you still nailed a great shot by being open-minded.
4. Bend and get eye-level with your subject. If you are standing straight and aiming camera downward, you will make your subject seem short and distorted. You have to get low and do an awkward mid-level slouch to get the best angle. (This is the most important thing you have to remember, it will drastically improve your shots.)
5. Shallow depth of field. It's so much nicer to look at a street style shot where the only thing in focus is the subject. Make sure to get familiar with your camera and learn your settings to master the "blurry" background.
Here are some links to my favorite street style photographers:
The Sartorialist
Garance Dore
Tommy Ton
Lee Oliveira
Amy Creyer