Camera bag for street photography and outdoor shooting

I think a tripod should be transported on a sling. Or left at home. Or left in the trunk of the car. Not strapped or lashed directly to or onto the camera bag. But maybe that's just me. I dunno...I got nothin' for you here except, "Lose the tripod".

I think the tripod should be left at home for street photography
 
I shoot lots of street photography and use the same bag as Bruce Gilden and Garry Winogrand will last for ever the Billingham Hadley Pro
 
It seems to me that the OP is looking for a one-size-fits-all-purposes bag. There isn't any such bags, in my opinion.

My shooting varies from church events other than weddings, to trains which may or may not require 'a hike' to get to a shooting location, or walking around in various downtown areas such as Chicago, or even riding transit such as the El in Chicago and getting shots from various platforms. What I carry varies widely depending on what I am shooting.

For those times that I can safely put my bag with 'the works' in it somewhere within, say, 100 feet of where I am shooting, then everything goes with me. Walking around in downtown areas, one camera with lens mounted, and 2nd lens in a Lowepro lens bag big enough to hold the bigger of the two lenses with me is on my belt. A small filter pouch is also on my belt. Carrying 20+ pounds of equipment for hours on end such as city shooting because I -might- want a different lens than what I have with me isn't practical, in my opinion. Either I failed to bring the 'right' two lenses with me that day or I can always go back another day with the 3rd lens.

In short, what are my 'carrying' requirements vs what can I safely leave somewhere close and access freely are at two ends of my bag needs. Planning ahead makes all the difference. Note that the word 'safely' above indicates free from accidental loss, damage, or theft.

Spot on.

Every bag, every backpack, every sling...is a compromise. It's about deciding what you want the carrying device to do.

1. I have a holster (Tamrac) that I use for street shooting, Inobtrusive, light, holds a body and 3 lens (but not my 200mm f2.8 zoom).
2. I have a photography backpack. Terrible for street shooting. But will hold a ton of gear and I can strap a tripod on to the side. It's great for schlepping gear from point A to point B. Terrible for wanting to shoot anything in between A and B.
3. I have a messenger bag. Handles my macAir, a body and a couple of lens (more than my holster). Can't handle a tripod.
4. I have a tactical vest. I often use this for shooting sports.
5. I have a camera bag insert from Timbuktu that I will put in to carry-on luggage or a backpack that I use when I have to carry two laptops plus a ton of other stuff. I've used this insert a lot.
6. I have a hiking backpack with multiple large compartments (so the camera gear isn't next to food which isn't next to wet clothes) that I use for adventure shoots and multi-day hikes. It works perfectly to strap a striped along side, and has the ergonomics to allow me to carry 60 pounds of crap/gear on my back for 3 days without needing surgery afterwards. I sometimes use parts of the Timbuktu insert with it.
7. When I fly all camera gear goes as carry-on into a soft-sided duffle bag with key toiletries (medicine), a few clothes (to act as padding), part of the Timbuktu insert,plus usually a soft box and a stand plus a backdrop.

I wouldn't part with any of these carrying devices. Love 'em all. Have used each one of them many times (well, not the messenger bag but that's b/c it's new). But when I use each one depends upon the circumstances. Is it just for carrying stuff or will I be pulling gear out to shoot and swapping out lens? What gear will I be taking? Are there padding or weather or safety/theft concerns?

To the OP, you're carrying an amazing amount of equipment for street shooting. if you're doing to carry that much stuff, I suggest you throw in a 42" x 72" reflector, a couple of speed lights, and maybe a soft box and light stand. I'm not being ridiculous. Most folks I've seen who are dedicated street photographers are defining it not just as shooting on the street but doing so very quickly, very little setup and staging, not a lot of equipment swapping. Usually it's two lens max (if that). If what you're really looking to do is to carry all of your gear and be able to access some of it quickly, then get an insert for your Thule and a good strap for your camera body with a decent zoom or the prime so you wear it on the outside. And then you'll have everything with you but can still shoot when something appears.
 

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