One of the biggest hurdles to overcome in street photography is inhibition. Taking candid photos of strangers is not for everyone. Your demeanor should be cool, calm, and confident, even if thats not how you feel inside.
Looking sheepish or, worse, creepy, is the last thing you want. The way you dress might have an effect. Rightly or wrongly, people will assess you based on their first impression. Think about ways you can blend in.
If confidence eludes you when... more