1. Wallet- I know this seems like a 'duh', however I've seen men who just throw their cash and cards in their pocket and I wonder how they don't lose things. Wallets come in many styles and whichever you choose is fine, as long as you use one. Debit/Credit cards, licenses and business cards belong in some holder. Cash can be held in same holder or in a clip as long as it's not just hanging loosely in your pocket.
2. Cell Phone- If you don't have one that's fine, but if you do then have it on you and ON! Whether it's on your belt or in your pocket it's important to have it with you when you leave the house; fully charged and the volume set to the appropriate level for your environment. The cell phone is a great tool in our society so why not have it ready on you when you need it.
3. Watch- This is a debatable item given cell phones tell the time too. But the importance is to have a way of telling time wherever you go so not having to ask those around you. I personally like the look and convenience of a watch so I use one.
4. Knife- Man's earliest tools was the knife, and what a versatile tool it is. Though given today's culture carrying a hunting knife into the store might get you some looks. That is why I recommend and carry a folding pocket knife, one that carries discretely in your pocket. Whether it's a tactical folder or an old fashion Buck knife every man needs to have a knife on him. From opening packages to defending yourself a knife is a must. Just be careful to not take it places that prohibit its carry: Court houses, amusement parks, some schools.
5. Pen and Paper- For someone like myself who easily forgets things the ability to take notes on the go is indispensable. Any pocket notebook will work but I recommend the Moleskine ruled notebooks, 2.5X4 inches. They're a little more in price but great due to their size. I use any half size pen I can find off the shelf.
The five items mentioned are a must for any gentleman's EDC. The following are optional but handy to have.
-Zippo Lighter- Not that I smoke but I sometimes carry a Zippo lighter for emergencies. It's a good tool for the rare occasions you need a fire. Though living in an urban environment the opportunity doesn't arise often, but it's there. They're also really cool.
-Eye Drops- If you wear contacts like me I don't leave home without contact re-wetting drops. A dry contact is easily lost.
-Flashlight- This should be on the list above but here it is, a key chain flashlight. A good LED light will help you when it's dark and you're trying to find the lock to your door.
So there you have it, my list of EDC for myself and every man. I use or used every item more than once in my daily life and I hope you can too. If I've missed something let me know, I'm open to new carries.