Whether on your bike or on your back. Do you like 'a place for everything and everything in it's place'? Or just a big gaping maw to dump/shove/stuff into?

I am trying to work it out so I can just lift stuff out of my panniers in plastic grocery bags and go. I still havent got it completely worked out.

My trunk bag ends up pretty full so needs a bit of organization. Wallet, keys and cell in first; clothes rolled up and in a plastic grocery sack on top of those; sunglasses and towel on top that. Everything else lives at work.

I have an order that I put things in the bag(Heaviest stuff on bottom) and try to not put stuff on the clothes to avoid wrinkles. But the only thing that has a dedicated place is the laptop.

Multiple pockets, a place for everything -- carryover from the military.

since the only thing that I actually need every day is my lunch, the rest of it (wallet, phone, memory sticks, pens, paper, probably a few other things) just sit in the bottom of the bag. There's not really that much there so it only takes 3 or 4 seconds to find something when I need it anyway.

I'm all for organization.

I TRY to keep my panniers organized, but it never seems to work out.

I usually am as well. But then there are sometimes when I don't want to have to put stuff away in their various pockets- I just want to stuff it and go. Or lately, I'll go to fetch something from a pocket/compartment, only to discover it went missing- because I decided to relocate it and forgot that I had moved it.

I put clothes in the bottom and lunch on top. A couple of times my shirt got a good whiff of balsamic vinaigrette. I've have since moved to "dry" salads.

Commuting by bike requires a certain amount of organization, but I still just stuff extra loads, work clothes, books,etc., wherever they fit.

I started with a backpack (GoLite Ion) that is just one big compartment. I put everything in there, but found that I spent time searching for my bike lock key & wallet to get into the office every day. I don't need much organization, but I switched to a backpack with one large pocket & one small pocket (for keys & wallet) and have been happy ever since.

I got a double pannier setup.
Left pannier contains: Lock, Lunch, Laundry (ie. used day clothes).
Right pannier contains everything else.

I find it's the easiest way to remember where stuff goes. Stuff that starts with "L" in the left, everything else on the right.
I assure you I have no OCD problems

Actually my method is a little of both of the above.

I have a EDC bag that goes every where I go, whether I ride, or drive. It is also one of the reasons I commute on a cargo bike, It is fairly organized, it has everything that I think I might want or need for the next three days. It generally rides in the drive side freeloader.

The left side freeloader holds my little black bag. It is one of those fabric shopping bags.

The little black bag has my bento box, my small thermos, my large thermos (both full on the way in), my coffee cup (can't get a holder that fits it, so it rides around empty), the book of the day, RainMates, personal water bottle for work, and snacks.

I would not be able to stuff my EDC bag into a pannier. The little black bag would be interesting to try to stuff in to a pannier.

When I get to work, I undo four buckles, grab the two bags, my battery and my hat, and am headed inside. In my mind a lot easier than loading and unloading panniers.

Since I'm using waterproof panniers I don't really have many options as they are just one big space with only a mesh pocket under the cover. I'm using smaller bags to organize things inside.

Depends on what you've got! Last year I had lots of cargo space and dumped everything under the sun in there. This year I' using no cargo capacity and carry a small backpack, even keeping the handlebars clear of extras, everything that I do carry has its place precisely.

Being gifted with ADD, I naturally tend toward extreme disorganization, but if I don't have some kind of system I end up not having everything I need. As a compromise, I've got a complete set of the usual take-along gear (tubes, tools, pump, etc.) that stays in each of my various bags and a moveable compartment that keeps the variable day needs (clothes and lunch) and move that to whatever bag I'm taking on a given day. So I guess I have a light organizational system within a overall dump-and-go system.

my cycling backpack has the one main storage compartment and a total of 7 separate pockets. i'm an "everything in its place" organizer. keys go here, wallet and phone go there, rain cover in this pocket, change of clothes in the main compartment, etc.

each of my bikes also has a small saddle bag with its own emergency roadside repair kit. i do that so i will ALWAYS have that stuff whether i'm riding with my backpack or not.

I use a rucksack from Ortlieb. Works great but I definitely have to think about how put things in. When changing in a bathroom at work i would rather reach in and have instant access to my clothes then pull out my lunch and thermos and having to set them somewhere in the stall while I find what I was really looking for (really wish we had a locker room).

gaping maw; I try to keep loose fruit separated from the lock though.

If I'm using my Banjo Brothers Expandable trunk bag with drop-down panniers or Axiom Seymor panniers, like to be organized. Everything has a place and it's in it's place. I can carry my lunch, clothes, reading material (book or nook) and items to get cleaned up at work.

Backpack here.
My only rules are that my repair kit and pump all be together in an outside pocket and that my laptop not be directly against my back. Everything else (including the laptop) goes into the bottomless maw.

gaping maw.

I'm considering this route, but take it one step further. I've found a backpack locally that is a top loader, internal frame, proper waist belt, sliding sternum strap, mesh back panel, compression straps... basically all the good stuff. It does lack the cycling specific goodies though of reflective bits, blinky tab, helmet holder, or even a rain cover.

I'm tempted to go pick it up tomorrow and take some measurements to see if this would fit to increase the organizational capacity some.

it's 4:00 am and I'm 10 yrs old maybe less. my siblings and I are bringing luggage down to the garage for my Dad to pack the car for our summer trip to the cape from new york. we were only allowed to bring the luggage to the car cuz Dad had to pack it just so. we were allowed some personal things in the cabin. I never wanted to be like that but I am.

I dream of dumping stuff in my rack truck but I know everything fits better when I think about it.