The only way to truly figure out what camera bag works best for you is to determine the gear you need (want) to have with you, when you leave the house/office.

Is it a full DSLR rig, with 2 bodies and all the glass? Or get small with a mirrorless system? Messenger bags take care of a certain type of shooting set-up, so if you really want to figure out your perfect (or near perfect) bag, take the gear you’ll be needing to carry down to your local brick and mortar camera store, and put your goodies into the proposed bag. And wear it. You’ll see soon enough what works for you.
It’s kinda like trying on a pair of shoes and walking around the store. Wouldn’t hurt to buy your bag from them, either. HAvinga good relationship with your local photo dealer is a great thing to have.
Of course, plenty of places online have good return policies. It’s your time and hassle for that effort. And make sure you can get to things like PhotoPlus Expo, to see and try em all.

The ThinkTank CityWalker 20 has been on my shoulder for almost 2 years now, because I pre-checked. This is a great lightweight, transformer, type of messenger bag, that has been designed by the pros at ThinkTank Photo, with the right amount of pockets, dividers, and comfort, that will bring you lots of use, both as a camera bag, and a daily bag. It’s perfect for street photography, and for the other 50% of your life, when you need to keep the weight and profile, low key.

It does come with one of the better made foam inserts, as a separate bucket with dividers,that velcros to the bottom of the bag. I personally don’t use it in the bag, but use it to build out shooting systems, and then store them safe and readily available.
I’m careful with my gear, but not precious.

So, on the inside are 2 interior pockets on either end with a velcro strap on top. In one, I always put a charging battery, and cable in there, and can add my phone, so I have a great little charging station.
In the other pocket, either a SpeedLight for a DSLR, or a 90mm lens, if going mirrorless.

There is an easy access pocket in the back, that is great for documents, and yes, some snacks. C’mon, sometimes standing at an event waiting on the key action, can make you a bit hungry. On the 2 outside side pockets, you have mesh, so easy to see what you have, and an elastic top to loosely secure whatever you put there.
Many times, I’ll put my sunglasses on one side, and a water bottle on the other. Or if I’m in a working situation, the speedlight may go there for easy access.
Plus, in the interior at the back, a zipped document section, that pretty well mirrors the outside pocket in size.

Then comes the magic front pockets. Each one has a good wide velcro strap to secure the goods in there, nice and tight.

The front pocket has all of the dividers you want: pens, LensPens (my fave lens cleaner), business cards (yep, people still use em), media card wallet connectors, and just some extra space. I can put a Fuji-X100T in that pocket and it is easy to access, and always at my fingertips.

The main body of the bag, I can put a Nikon D810 with a 24-70, 70-200mm, OR a sweet 28-300, with room to spare. Plus a smaller prime.
Going mirrorless? OK, a Fuji X-T1 with grip and a 56mm, a 55-140 in the side pocket, and a 14mm on its own. A little light configuration.I can put batteries in one of the front pockets, but more often than not, they are in my pants pockets.

The flap has the ThinkTank silent velcro option, and a buckle, so you can either go loose closure, or the tighter, noisy velcro. Yep, I’m always in silent mode. In addition the top flap has a zipper pocket, for docs or small items. I put a plastic bag with aspirin, wipes,gum, sunscreen packets, chapstick, etc.

The strap is well made, with a good wide webbing, and the shoulder “grip” is adjustable and stay where you want it. They added a thin hand carry strap, and it has come in handy, especially when taking a sit break.And there is also a business card clear window holder, so when you leave it somewhere, people can find you. Don’t ask.

You can tell i have a lot to say about this bag as I’ve used it for over 2 years. It has the high quality that ThinkTank Photo bags all have, and as a lightweight, soft, bag, it’s usually the first bag I reach for when going out on a walk.

from the folks who made it:

And here is a video portrait from ThinkTank on one of their CityWalker users:

What I don’t do with it, is add a tablet or MacBook Air. When this bag has that added weight, plus a power cord/block, the loose structure is not the best for me. So, this does not become my bag for all-in-one office in a bag use.
I have, in the past, moved to a backpack for that added weight. Like the ThinkTank Perception 15. A great working backpack, that I grew to love. More for the versatility, than as a perfect camera bag. Right tool, for right job.
What I carried on July 4th: Fuji X100T (23mm f/2) Fuji X-T1 with a 55-140 zoom, Fuji 14mm, batteries, cards, water bottle, moleskin notebook, Theta S 360º camera, brimmed hat, snacks, lenspen, media car wallet, small gorillapod tripod, with giotto head, phone charger, with cable, business card case, and press credentials.

Oh, here is a shot from the Theta S at Deno’s Wonder Wheel Arcade

Post from RICOH THETA. #theta360 – Spherical Image – RICOH THETA

For about $100, this bag is a strong recco. One that should be in your repertoire.

Next up, the bag that does it all.