Gandalf, Captain Picard and Santa Claus

I carry a wallet, a pen, a chapstick, a flash drive on a neck lanyard, a smartphone, a pliers-based multitool, my keys and a lighter.

I also, as a rule, always wear shoes that I can run in. So I select dress shoes carefully.

When I moved to China I added a pack of tissues to my bag - most bathrooms don't provide TP.

My phone stays clipped to my jeans. My purse has a built-in wallet for cash, checkbook (with pen), and necessary cards. Other than that, it holds car keys, a comb, grocery coupons, hair ties, and some candy. My car has a toolbox, jumper cables, grocery bags, and mosquito repellant.

I hate having stuff in my pockets, and my keys kept wearing holes in them. I finally settled on a system that is similar to the CERN Lecture Belt, but my family calls it the "Geek Belt". It is a nylon web belt on which I clip carabiners for holding a key ring and a USB Flash drive with a number of useful utilities, files and a couple of operating systems (it's a bootable drive). There's a case for my phone and also a larger case to hold a palmtop, my ID and credit cards. I also keep a knife clipped to it.

I carry stuff in a fanny pack on the weekends and get picked on for it. I still do it anyway.

Fanny pack: reading glasses; pen; cell; camera; meds; pepper spray and tissues.
Pockets: wallet; pen knife; keys with USB; second wallet for any criminals that happen by; chap stick; clip knife in my waistband.

By now you realize I live in the city :) I'd carry a gun, but it's against the law here and they say the police are supposed to protect me.

pockets: Taxi Wallet, cell-phone, keys.
backpack: LLBean Turbo Transit backpack (black), external hard drive in case logic case (with ipod/usb connector), headphones, a couple of books, pens, 2nd gen ipod touch, pen shaped mini screwdriver, Altoid tin with extra screw tips and other effluvia, mouse, Lenovo laptop (so the kid doesn't wash this one with a bottle of water, like the last laptop).... and random parts of toys from the 5 year old (stuff i almost stepped on). I'm slowly working on creating a mobile office in a backpack. Hopefully (and slowly given my limited extra income), i'll be able to condense/add a few things to make it a small office i can carry on my back.