I have two "levels" of camera bags when/if I pack a bag to actually carry around with me while shooting.
One bag is a small men's shaving bag with a shoulder strap. It has a big top-loading pocket with a dual-zipper flap, a velcro divider in the main compartment, and a side zipper pocket.
The side pocket has business cards, pens, pencils, Sharpies, a retractable brush, lens caps, sometimes filters, sometimes film if I need to make some room in the main pocket. There is a small cable release in there as well and an old mechanical delay for it, though I rarely use either. Sometimes batteries go in here as well, and CF cards when needed. Sometimes I put my Brockway (Sekonic) incident meter in there for quicker access.
The main pocket usually carries a lens on one side and film on the other, and a light meter (or two), though it has been rearranged every which way that I can imagine. I have even put camera bodies there, and occasionally a speedlight.
This is usually the bag I use.
The other bag is at least twice as big. It is an Amvona bag (read CHEEPIE) that was given to me by a friend a few years back. It has a deep main pocket with a velcro divider or two. It has two big side pockets, a zippered mesh net above the main pocket, a front zippered pocked on the top, a front zippered pocket on the body, etc. I like that you can really stuff a lot of crap into it, even though it is not a huge-looking bag. I use it for when I might be going on a short trip, when I simply need to carry more than the shaving bag will fit, or sometimes when I am walking around using medium format instead of small format.
I have several stepping rings and some filters, cable releases, tape, Sharpies, cards, a brush, and usually lots and lots of film.
When on a big trip, both of these are usually "satellite" bags to the main bags and cases that are used for storage of the equipment.
"Truth and love are my law and worship. Form and conscience are my manifestation and guide. Nature and peace are my shelter and companions. Order is my attitude. Beauty and perfection are my attack."
- Rob Tyner (1944 - 1991)
Well, I'm in the 2 bag arena as well: the first is always a Zeiss Ikon related (small) bag, now filled with a Ikonta postwar with Tessar, a Gossen Sixtomat digital, a sunshade, a Watameter and a booklet/pen to make some notes (if necessary).
The second bag is somewhat larger and contains (today) a Canon T90, FD 2/35, FD 3.5/35-105, FD 2.8/20, Cokin A system with some 10 filters.
I have two camera bags. One has a Fuji S7000 digital and it's stuff, memory cards, etc. The other has my old gear, a Pentax SP1 that's unfortunately in pretty bad shape, and a black Canon AE-1, several lenses, filters, film, flashes, etc.
I just came back from some street shooting I was carrying a Canon EF with a FD 35mm f2 lens attached in a small Lowe pro Top loader bag that contained spare batteries the hood for the lens on a Lowe pro waist belt that also has on it a Think Tank pouch that contains FD20mm f2.8 lens with hood, and a Sekonic L-358 meter plus two spare rolls of Fuji Provia, I keep my gear simple for shooting street.
Last weekend I went out with a Pentax Spotmatic F, 50mm f1.4 SMC Tak, Asanamua 21mm f3.8, and Vivitar 200mm f3.5.
I also had an extra sr44 battery, a Gossen Luna-pro which I used for a couple of shots, and both warming and cooling filters for the Tak.
1 roll Kodak Ektar 100.
All in a soft leather shoulder bag with some buble-wrap on the bottom for extra cushoning.
Film is being developed.
Go not to the elves for counsel, for they will say both yes and no.
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I'm on my way out for a days shooting It's a very warm sunny day,and don't want to lug too much gear, I'm taking a Canon T90 with FD 20mm f2.8, 35mm f2 and a Vivitar Series 1 70-210 f3.5 zoom , five rolls of Fuji Velvia 100 , and a Sekonic L-358 meter with the 1 degree spot attachment, all in a Billingham 335 bag.
I don't bring a bag...
...unless I'm shooting a wedding. Normal shooting I just go out with one camera with one lens and an extra roll of film or battery.
On bike, I'll bring the Nikon FE with slow film and a 24 2.8 for landscapes.
Out with friends I'll bring the Nikon N80 with 400 Tri-X and a 50 1.8 for candids.
Chasing grandkids I'll bring the Canon T2i and a 50 1.4 for shooting video and stills.
Shooting low-light city shots I bring the Nikon D700 and a 50 1.8.
I stopped carrying camera bags a long time ago. I usually bring 1 to 3 cameras with lenses that I might want to use and my incident meter.
(I do keep a lot of extras in my trunk... film cooler, tripods, monopods, batteries, darkbag, spare gear, etc.)
Two Leica M6 classic bodies, one silver, one black, two 50mm Summicrons and a 35mm Summicron. Lots of film and a Moleskine notebook.
I gave up on a bag some time ago. I used to hike a lot more than I do now, and I carried whatever pocket digital point and shoot I was not going to worry about destroying, so I got in the habit of working with very little. When I decided to take the plunge and just bring an SLR and live with it if I ruined it I was using a Kodak C310 and was getting great shots so I know I can deal with not having a huge setup with me.
When I go out these days, I have three setups I like to use, also I wear a Camelbak backpack with water, clothing, and I will toss in any gear I am not using, lenses, flash, filters etc. if I have it. I sometimes toss in a spare specialty camera, 3D, Brownie folder, point and shoot digital, or something fun like that.
If I have been there before I bring a camera set up with a lens and filters for what I believe I will do the most of that day, and some extra film, and a flash only if I know I will need it.
If I have not been there before, or shooting will be varied I bring a camera with a general set up like a Nikon film camera with two or three speeds of film, or maybe the D70 with 18-200mm zoom lens, and a flash.
If it will be wet I bring my Nikonos V with the 35mm, and some faster film as the flash set up on that camera just looks silly, if I will be underwater I bring the flash and slower film because I will need it.
I can do a lot with next to nothing so I am lucky that I don't need to carry a large kit for what I do, also I am not a pro so time is not money for me. I have the gear that will allow me to compose a shot quickly and I do use it when I need to do that, but if I don't have the exact gear I need to get a shot, generally I can do quite well with the gear I have with me.