I shoot a lot of Street. Over the years I have developed a bit of a philosophy about shooting Street. One of my attractions to photography and to Street, is the challenge. There is always something new to learn and always the challenge of capturing the exceptional image. For me, one of the challenges of Street is not to camouflage, be stealthy or sneaky when shooting but to mentally blend into the street.
Part of my philosophy is to shoot Street with respect. The Street isn't a zoo for the amusement of outsiders. It is the front yard, the backyard, it is where people work, play, eat, socialize ... it is their home. I feel that if I am respectful to the the Street then the Street would be inclined to treat me similarly. Dress is the first step in that thinking. I dress as I would when I was a news photog ... collared shirt (no tank or tees and no writing or images), long pant (nice jeans or khakis), closed toe shoe (no sandals). My prefered shooting is with two camera and a bag and that's what I take to the Street. I shoot with the viewfinder. I want to give the impression that I am a professional, that I have a reason to be there, that I am working ... just like themselves.
A bit of a long winded way of getting to dress, but I just felt greater detail was required. Again, for me the trick in shooting Street is to blend in, to be a part of the Street, to be no different than the lamp post or news stand. (I'm not judging those who shoot from the hip or differently than I. We all see differently and we all shoot differently.)
As to vests, I have a Domke vest. I use sometimes use for events, especially long events when I'm on my feet shooting for hours at a time.