I'll start with what I typically wear most days: my clothes on a typical day are cargo pants, a plain short-sleeve shirt in summer or plain sweatshirt in winter, and a pair of hiking shoes. When needed, I wear a plain hoodie or heavier coat. The ideas behind the way I dress are: 1) comfortable, ease-of-movement; 2) rugged; 3) practical, utilitarian; 3) not flashy or eye-catching; 4) and fits in fairly well with what other locals are likely to wear. (On the rare occasions I have to "dress up," I'll alter my EDC appropriately.)
Now, for the pocket dump:
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Also on my belt, I carry a Bushnell LED flashlight. I've been carrying this one for over a month now, and generally like it. However, I wish it had a bit more battery life. It has over 5 hours on low (13 lumens), but only 50 minutes on high (140 lumens). If you have a suggestion for a good, compact EDC flashlight, please leave it in the comments below.
In my right front pocket, I carry my Maxpedition Urban Wallet (not pictured) and about $2 in quarters. I front-carry my wallet because it is much more difficult for a pick-pocket to steal from a front pocket than a rear pocket.
In my left front pocket, I carry my Swiss Army Knife, "Hiker" model. I also carry my keys in this pocket. On my key chain, I have my keys, an extremely rugged Gorilla Drive flash drive (I encrypt personal files on it with Rohos encryption software), and a Gerber Shard mini pry bar (with screwdrivers and bottle opener).
In my right cargo pocket, I carry my cell phone (not pictured). I also carry my personalized organizational system (some index cards held together with a binder clip) for keeping lists, taking notes, leaving messages, etc., and a reliable pen.
In my left cargo pocket, I carry my Kershaw Lifter folding knife and a Maxpedition micro pocket organizer (pictured below).
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I use the pocket organizer primarily as a personal first aid kit, with a couple of other items , too. On the outside pocket, I carry a couple of individually wrapped Wet Ones, useful for cleaning hands before eating, but can also be used to clean other things. The first aid supplies include wound care items (alcohol wipes, iodine wipes, a couple of packets of triple antibiotic ointment, several sizes and styles of bandages, and a small pack of quick clout), Uncle Bill's Silver Gripper tweezers (for removing bee stingers, ticks, splinters, etc.), insect sting relief, benedryl caplets, aspirin, advil, aleve, and a couple of packets of electrolytes to add to water.
Also in the kit is a twenty-dollar bill, a small roll of duct tape, a couple of six inch strips of orange duct tape, an Eat-N-Tool by CRKT, a pair of fingernail clippers, a brass 3-inch safety pin, and a Leatherman Style CS Multi-tool (a great pair of folding scissors).
Yes. Everything pictured fits easily into the organizer, with a little room to spare.
Other Items (not pictured)
My sunglasses are with me constantly. I also wear a Celtic Cross on a chain around my neck. And I carry a bandanna in my back pocket.