The work bag or briefcase you carry when you walk into the office, a meeting or a restaurant says something about you and your style. So we always opt for a timeless style that's durable enough to take your daily abuse, but stylish enough to look right in any occasion. But just like in life, it's what's on the inside that really counts. And in the limited space of a man's bag, the less he has to tote around the better.

Keep a mindful eye on your carryall's contents. Once a week, take everything out of your bag, flip it upside down to shake out any dust, dirt and inexplicable debris that has accumulated. Next, look at your stuff—toss any items that haven't been touched for a week or two. There's nothing cool about rooting through a dirty, cluttered bag when you're trying to locate a pen or your business card. That being said, there are a few items that every man should have on hand at all times.